Upland Software (UPLD) 10-Q 1 Aug 24 2024 Q2 Quarterly report Financial data

Cover

Cover - shares	6 Months Ended
	Jun. 30, 2024	Jul. 30, 2024
Document Information [Line Items]
Document Type	10-Q
Document Quarterly Report	true
Document Period End Date	Jun. 30, 2024
Document Transition Report	false
Entity File Number	001-36720
Entity Registrant Name	UPLAND SOFTWARE, INC.
Entity Incorporation, State or Country Code	DE
Entity Tax Identification Number	27-2992077
Entity Address, Address Line One	401 Congress Ave., Suite 1850
Entity Address, City or Town	Austin
Entity Address, State or Province	TX
Entity Address, Postal Zip Code	78701
City Area Code	512
Local Phone Number	960-1010
Entity Current Reporting Status	Yes
Entity Interactive Data Current	Yes
Entity Filer Category	Accelerated Filer
Entity Small Business	false
Entity Emerging Growth Company	false
Entity Shell Company	false
Entity Common Stock, Shares Outstanding		27,265,746
Entity Central Index Key	0001505155
Current Fiscal Year End Date	--12-31
Document Fiscal Year Focus	2024
Document Fiscal Period Focus	Q2
Amendment Flag	false
Common Stock
Document Information [Line Items]
Title of 12(b) Security	Common Stock, par value $0.0001 per share
Trading Symbol	UPLD
Security Exchange Name	NASDAQ
Preferred Stock Purchase Rights
Document Information [Line Items]
Title of 12(b) Security	Preferred Stock Purchase Rights
No Trading Symbol Flag	true
Security Exchange Name	NASDAQ

Condensed Consolidated Balance

Condensed Consolidated Balance Sheets - USD ($) $ in Thousands	Jun. 30, 2024	Dec. 31, 2023
Current assets:
Cash and cash equivalents	$ 232,375	$ 236,559
Accounts receivable (net of allowance of $383 and $572 at June 30, 2024, and December 31, 2023, respectively)	30,242	38,765
Deferred commissions, current	9,369	10,429
Unbilled receivables	3,531	2,701
Income tax receivable, current	4,803	3,775
Prepaid expenses and other current assets	9,609	8,004
Total current assets	289,929	300,233
Tax credits receivable	1,176	1,657
Property and equipment, net	1,768	1,932
Operating lease right-of-use asset	2,029	2,929
Intangible assets, net	152,896	182,349
Goodwill	264,164	353,778
Deferred commissions, noncurrent	12,602	12,568
Interest rate swap assets	14,933	14,270
Other assets	358	308
Total assets	739,855	870,024
Current liabilities:
Accounts payable	7,483	8,137
Accrued compensation	8,445	7,174
Accrued expenses and other current liabilities	6,244	7,050
Deferred revenue	95,066	102,763
Operating lease liabilities, current	1,732	2,351
Current maturities of notes payable (includes unamortized discount of $2,087 and $2,228 at June 30, 2024, and December 31, 2023, respectively)	3,313	3,172
Total current liabilities	122,283	130,647
Notes payable, less current maturities (includes unamortized discount of $2,201 and $3,148 at June 30, 2024, and December 31, 2023, respectively)	471,749	473,502
Deferred revenue, noncurrent	3,146	3,860
Operating lease liabilities, noncurrent	969	1,597
Noncurrent deferred tax liability, net	14,358	16,025
Other long-term liabilities	459	461
Total liabilities	612,964	626,092
Mezzanine equity:
Series A Convertible Preferred stock, $0.0001 par value; 5,000,000 shares authorized; 115,000 shares issued and outstanding as of June 30, 2024, and December 31, 2023, respectively	120,403	117,638
Stockholders’ equity:
Common stock, $0.0001 par value; 75,000,000 shares authorized; 27,265,746 and 29,908,407 shares issued and outstanding as of June 30, 2024, and December 31, 2023, respectively	3	3
Additional paid-in capital	603,526	608,995
Accumulated other comprehensive income (loss)	(600)	6,168
Accumulated deficit	(596,441)	(488,872)
Total stockholders’ equity	6,488	126,294
Total liabilities, convertible preferred stock and stockholders’ equity	$ 739,855	$ 870,024

Condensed Consolidated Balanc_2

Condensed Consolidated Balance Sheets (Parenthetical) - USD ($) $ in Thousands	Jun. 30, 2024	Dec. 31, 2023
Statement of Financial Position [Abstract]
Accounts receivable, allowance for credit loss, current	$ 383	$ 572
Unamortized discount, current	2,087	2,228
Unamortized discount, noncurrent	$ 2,201	$ 3,148
Series A convertible preferred stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Series A convertible preferred stock, authorized (in shares)	5,000,000	5,000,000
Series A convertible preferred stock, issued (in shares)	115,000	115,000
Series A convertible preferred stock, outstanding (in shares)	115,000	115,000
Common stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Common stock authorized (in shares)	75,000,000	75,000,000
Common stock issued (in shares)	27,265,746	29,908,407
Common stock outstanding (in shares)	27,265,746	29,908,407

Condensed Consolidated Statemen

Condensed Consolidated Statements of Operations (unaudited) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2024	Jun. 30, 2023	Jun. 30, 2024	Jun. 30, 2023
Revenue	$ 69,339	$ 74,497	$ 140,075	$ 151,553
Cost of revenue	20,474	24,178	41,523	49,714
Gross profit	48,865	50,319	98,552	101,839
Operating expenses:
Sales and marketing	16,791	15,755	33,809	30,044
Research and development	12,185	12,443	24,640	24,973
General and administrative	13,880	15,583	27,112	32,772
Depreciation and amortization	11,380	14,853	22,776	29,947
Acquisition-related expenses	0	1,072	0	2,166
Impairment of goodwill	0	0	87,227	128,755
Total operating expenses	54,236	59,706	195,564	248,657
Loss from operations	(5,371)	(9,387)	(97,012)	(146,818)
Other expense:
Interest expense, net	(5,056)	(5,376)	(10,014)	(10,837)
Other income (expense), net	198	(617)	120	808
Total other expense	(4,858)	(5,993)	(9,894)	(10,029)
Loss before benefit from (provision for) income taxes	(10,229)	(15,380)	(106,906)	(156,847)
Benefit from (provision for) income taxes	(1,210)	233	(663)	1,655
Net loss	(11,439)	(15,147)	(107,569)	(155,192)
Preferred stock dividends	(1,390)	(1,329)	(2,765)	(2,644)
Net loss attributable to common stockholders, basic	(12,829)	(16,476)	(110,334)	(157,836)
Net loss attributable to common stockholders, diluted	$ (12,829)	$ (16,476)	$ (110,334)	$ (157,836)
Net loss per common share:
Net loss per common share, basic (in dollars per share)	$ (0.47)	$ (0.51)	$ (3.92)	$ (4.88)
Net loss per common share, diluted (in dollars per share)	$ (0.47)	$ (0.51)	$ (3.92)	$ (4.88)
Weighted-average common shares outstanding, basic (in shares)	27,348,672	32,473,872	28,133,285	32,367,084
Weighted-average common shares outstanding, diluted (in shares)	27,348,672	32,473,872	28,133,285	32,367,084
Total product revenue
Revenue	$ 67,234	$ 71,746	$ 135,782	$ 146,231
Subscription and support
Revenue	65,504	70,494	132,582	143,408
Cost of revenue	19,247	22,073	39,076	45,558
Perpetual license
Revenue	1,730	1,252	3,200	2,823
Professional services
Revenue	2,105	2,751	4,293	5,322
Cost of revenue	$ 1,227	$ 2,105	$ 2,447	$ 4,156

Condensed Consolidated Statem_2

Condensed Consolidated Statements of Comprehensive Income (Loss) (unaudited) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2024	Jun. 30, 2023	Jun. 30, 2024	Jun. 30, 2023
Statement of Comprehensive Income [Abstract]
Net loss	$ (11,439)	$ (15,147)	$ (107,569)	$ (155,192)
Other comprehensive income (loss):
Foreign currency translation adjustment	(208)	840	(2,819)	855
Unrealized translation gain (loss) on foreign currency denominated intercompany loans, net of taxes	(258)	2,464	(1,670)	3,699
Interest rate swaps	(2,441)	7,905	(2,279)	(249)
Other comprehensive income (loss):	(2,907)	11,209	(6,768)	4,305
Comprehensive loss	$ (14,346)	$ (3,938)	$ (114,337)	$ (150,887)

Condensed Consolidated Statem_3

Condensed Consolidated Statements of Equity (unaudited) - USD ($) $ in Thousands	Total	Common Stock	Additional Paid-In Capital	Accumulated Other Comprehensive Income (Loss)	Accumulated Deficit
Beginning balance (in shares) at Dec. 31, 2022	115,000
Beginning balance at Dec. 31, 2022	$ 112,291
Increase (Decrease) in Temporary Equity [Roll Forward]
Dividends accrued - Convertible Preferred Stock	$ 2,644
Ending balance (in shares) at Jun. 30, 2023	115,000
Ending balance at Jun. 30, 2023	$ 114,935
Beginning balance (in shares) at Dec. 31, 2022		32,221,855
Beginning balance at Dec. 31, 2022	308,870	$ 3	$ 606,755	$ 11,110	$ (308,998)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Dividends accrued - Convertible Preferred Stock	(2,644)		(2,644)
Issuance of stock under Company plans, net of shares withheld for tax (in shares)		432,760
Issuance of stock under Company plans, net of shares withheld for tax	(387)		(387)
Stock-based compensation	12,832		12,832
Foreign currency translation adjustment	855			855
Unrealized translation gain (loss) on intercompany loans with foreign subsidiaries	3,699			3,699
Interest rate swaps	(249)			(249)
Net loss	(155,192)				(155,192)
Ending balance (in shares) at Jun. 30, 2023		32,654,615
Ending balance at Jun. 30, 2023	$ 167,784	$ 3	616,556	15,415	(464,190)
Beginning balance (in shares) at Mar. 31, 2023	115,000
Beginning balance at Mar. 31, 2023	$ 113,606
Increase (Decrease) in Temporary Equity [Roll Forward]
Dividends accrued - Convertible Preferred Stock	$ 1,329
Ending balance (in shares) at Jun. 30, 2023	115,000
Ending balance at Jun. 30, 2023	$ 114,935
Beginning balance (in shares) at Mar. 31, 2023		32,441,010
Beginning balance at Mar. 31, 2023	166,833	$ 3	611,667	4,206	(449,043)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Dividends accrued - Convertible Preferred Stock	(1,329)		(1,329)
Issuance of stock under Company plans, net of shares withheld for tax (in shares)		213,605
Issuance of stock under Company plans, net of shares withheld for tax	(152)		(152)
Stock-based compensation	6,370		6,370
Foreign currency translation adjustment	840			840
Unrealized translation gain (loss) on intercompany loans with foreign subsidiaries	2,464			2,464
Interest rate swaps	7,905			7,905
Net loss	(15,147)				(15,147)
Ending balance (in shares) at Jun. 30, 2023		32,654,615
Ending balance at Jun. 30, 2023	$ 167,784	$ 3	616,556	15,415	(464,190)
Beginning balance (in shares) at Dec. 31, 2023	115,000
Beginning balance at Dec. 31, 2023	$ 117,638
Increase (Decrease) in Temporary Equity [Roll Forward]
Dividends accrued - Convertible Preferred Stock	$ 2,765
Ending balance (in shares) at Jun. 30, 2024	115,000
Ending balance at Jun. 30, 2024	$ 120,403
Beginning balance (in shares) at Dec. 31, 2023	29,908,407	29,908,407
Beginning balance at Dec. 31, 2023	$ 126,294	$ 3	608,995	6,168	(488,872)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Dividends accrued - Convertible Preferred Stock	(2,765)		(2,765)
Issuance of stock under Company plans, net of shares withheld for tax (in shares)		566,044
Issuance of stock under Company plans, net of shares withheld for tax	(563)		(563)
Stock repurchases and retirements (in shares)		(3,208,705)
Stock repurchases and retirements	(10,796)		(10,796)
Stock-based compensation	8,655		8,655
Foreign currency translation adjustment	(2,819)			(2,819)
Unrealized translation gain (loss) on intercompany loans with foreign subsidiaries	(1,670)			(1,670)
Interest rate swaps	(2,279)			(2,279)
Net loss	$ (107,569)				(107,569)
Ending balance (in shares) at Jun. 30, 2024	27,265,746	27,265,746
Ending balance at Jun. 30, 2024	$ 6,488	$ 3	603,526	(600)	(596,441)
Beginning balance (in shares) at Mar. 31, 2024	115,000
Beginning balance at Mar. 31, 2024	$ 119,013
Increase (Decrease) in Temporary Equity [Roll Forward]
Dividends accrued - Convertible Preferred Stock	$ 1,390
Ending balance (in shares) at Jun. 30, 2024	115,000
Ending balance at Jun. 30, 2024	$ 120,403
Beginning balance (in shares) at Mar. 31, 2024		27,996,656
Beginning balance at Mar. 31, 2024	20,121	$ 3	602,813	2,307	(585,002)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Dividends accrued - Convertible Preferred Stock	(1,390)		(1,390)
Issuance of stock under Company plans, net of shares withheld for tax (in shares)		235,141
Issuance of stock under Company plans, net of shares withheld for tax	(232)		(232)
Stock repurchases and retirements (in shares)		(966,051)
Stock repurchases and retirements	(2,798)		(2,798)
Stock-based compensation	5,133		5,133
Foreign currency translation adjustment	(208)			(208)
Unrealized translation gain (loss) on intercompany loans with foreign subsidiaries	(258)			(258)
Interest rate swaps	(2,441)			(2,441)
Net loss	$ (11,439)				(11,439)
Ending balance (in shares) at Jun. 30, 2024	27,265,746	27,265,746
Ending balance at Jun. 30, 2024	$ 6,488	$ 3	$ 603,526	$ (600)	$ (596,441)

Condensed Consolidated Statem_4

Condensed Consolidated Statements of Cash Flows (unaudited) - USD ($) $ in Thousands	6 Months Ended
	Jun. 30, 2024	Jun. 30, 2023
Operating activities
Net loss	$ (107,569)	$ (155,192)
Adjustments to reconcile net loss to net cash provided by operating activities:
Depreciation and amortization	27,599	36,784
Deferred income taxes	(1,176)	(2,674)
Amortization of deferred costs	6,076	6,667
Foreign currency re-measurement gain	(694)	(882)
Non-cash interest, net and other income, net	(1,776)	1,152
Non-cash stock-based compensation expense	8,655	12,832
Non-cash loss on impairment of goodwill	87,227	128,755
Non-cash loss on retirement of fixed assets	18	34
Changes in operating assets and liabilities, net of purchase business combinations:
Accounts receivable	8,362	13,212
Prepaid expenses and other current assets	(3,603)	(1,649)
Other assets	(4,907)	(4,875)
Accounts payable	(613)	(1,217)
Accrued expenses and other liabilities	706	(4,106)
Deferred revenue	(7,714)	(5,994)
Net cash provided by operating activities	10,591	22,847
Investing activities
Purchase of property and equipment	(457)	(504)
Net cash used in investing activities	(457)	(504)
Financing activities
Payments of debt costs	(77)	(177)
Payments on notes payable	(2,700)	(2,700)
Stock repurchases and retirement	(10,958)	0
Taxes paid related to net share settlement of equity awards	(563)	(388)
Issuance of common stock, net of issuance costs	0	1
Additional consideration paid to sellers of businesses	0	(5,550)
Net cash used in financing activities	(14,298)	(8,814)
Effect of exchange rate fluctuations on cash	(20)	374
Change in cash and cash equivalents	(4,184)	13,903
Cash and cash equivalents, beginning of period	236,559	248,653
Cash and cash equivalents, end of period	232,375	262,556
Supplemental disclosures of cash flow information:
Cash paid for interest, net of interest rate swaps	17,565	14,426
Cash paid for taxes	$ 3,162	$ 4,972

Organization and Nature of Oper

Organization and Nature of Operations	6 Months Ended
	Jun. 30, 2024
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Organization and Nature of Operations	1. Organization and Nature of Operations Upland Software, Inc. (“Upland,” “we,” “us,” “our,” or the “Company”), a Delaware corporation, enables global businesses to work smarter with over 25 cloud software products that help increase revenue, reduce costs, and deliver business value. Upland's solutions offer many integrated AI capabilities and cover digital marketing, knowledge management, contact center service, sales productivity, and content lifecycle automation. Upland services over 10,000 customers ranging from large global corporations and various government agencies to small and medium-sized businesses. The Company's customers operate in a wide variety of industries, including financial services, consulting services, technology, manufacturing, media, telecommunications, government, insurance, non-profit, healthcare, life sciences, retail, and hospitality.

Basis of Presentation and Summa

Basis of Presentation and Summary of Significant Accounting Policies	6 Months Ended
	Jun. 30, 2024
Accounting Policies [Abstract]
Basis of Presentation and Summary of Significant Accounting Policies	2. Basis of Presentation and Summary of Significant Accounting Policies Basis of Presentation These condensed consolidated financial statements have been prepared in conformity with accounting principles generally accepted in the United States (“GAAP”). The condensed consolidated financial statements include the accounts of Upland Software, Inc. and its wholly owned subsidiaries (collectively referred to as “Upland”, the “Company”, “we”, “us” or “our”). All intercompany accounts and transactions have been eliminated in consolidation. No material changes have been made to the Company’s significant accounting policies disclosed in Note 2, Basis of Presentation and Summary of Significant Accounting Policies , in our Annual Report. The accompanying unaudited interim condensed consolidated financial statements have been prepared pursuant to the rules and regulations of the Securities and Exchange Commission (the “SEC”) for interim financial reporting. In the opinion of management of the Company, the unaudited interim condensed consolidated financial statements have been prepared on the same basis as the audited consolidated financial statements, in all material respects, and include all adjustments of a normal recurring nature necessary for a fair presentation. The results of operations for the six months ended June 30, 2024 are not necessarily indicative of the results to be expected for the year ending December 31, 2024 or for any other period. The financial statements should be read in conjunction with the consolidated financial statements and notes thereto included in the Company’s 2023 Annual Report on Form 10-K filed with the SEC on February 22, 2024. Use of Estimates The preparation of the accompanying condensed consolidated financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities, disclosure of contingent assets and liabilities at the date of the condensed consolidated financial statements, and the reported amounts of revenues and expenses. Significant items subject to such estimates include those related to revenue recognition, deferred commissions, allowance for credit losses, stock-based compensation, contingent consideration, acquired intangible assets, impairment of goodwill, intangibles and long-lived assets, the useful lives of intangible assets and property and equipment, the fair value of the Company’s interest rate swaps and income taxes. In accordance with GAAP, management bases its estimates on historical experience and on various other assumptions that management believes are reasonable under the circumstances. Management regularly evaluates its estimates and assumptions using historical experience and other factors; however, actual results could differ from those estimates. Upland is not aware of any specific event or circumstance that would require an update to its estimates or judgments or a revision of the carrying value of its assets or liabilities as of August 1, 2024, the date of issuance of this Quarterly Report on Form 10-Q. These estimates may change as new events occur and additional information is obtained. Actual results could differ materially from these estimates under different assumptions or conditions. Concentrations of Credit Risk and Significant Customers Financial instruments that potentially subject the Company to credit risk consist of cash and cash equivalents, accounts receivable and the Company’s interest rate swap hedges. The Company’s cash and cash equivalents are placed with high quality financial institutions, which, at times, may exceed federally insured limits. The Company has not experienced any losses in these accounts, and the Company does not believe it is exposed to any significant credit risk related to cash and cash equivalents. The Company provides credit, in the normal course of business, to a number of its customers and generally does not require collateral. To manage accounts receivable credit risk, the Company performs periodic credit evaluations of its customers and maintains current expected credit losses which considers such factors as historical loss information, geographic location of customers, current market conditions, and reasonable and supportable forecasts. No individual customer represented more than 10% of total revenues for the six months ended June 30, 2024, or more than 10% of accounts receivable as of June 30, 2024 or December 31, 2023. Recent Accounting Pronouncements Recently issued accounting pronouncements - Not Adopted In November 2023, the FASB issued ASU 2023-07, Segment Reporting (Topic 280): Improvements to Reportable Segment Disclosures , which requires public entities to disclose information about their reportable segments' significant expenses and other segment items on an interim and annual basis. Public entities with a single reportable segment are required to apply the disclosure requirements in ASU 2023-07, as well as all existing segment disclosures and reconciliation requirements in ASC 280 on an interim and annual basis. ASU 2023-07 is effective for fiscal years beginning after December 15, 2023, and for interim periods within fiscal years beginning after December 15, 2024, with early adoption permitted. ASU 2023-07 should be applied on a retrospective basis. The Company is currently evaluating the impact of adopting ASU 2023-07 on its disclosures. In December 2023, the FASB issued ASU 2023-09, Income Taxes (Topic 740): Improvements to Income Tax Disclosures , which requires public entities, on an annual basis, to provide disclosure of specific categories in the rate reconciliation, as well as disclosure of income taxes paid disaggregated by jurisdiction. ASU 2023-09 is effective for fiscal years beginning after December 15, 2024, with early adoption permitted. ASU 2023-09 should be applied on a prospective basis, and retrospective application is permitted. The Company is currently evaluating the impact of adopting ASU 2023-09 on its disclosures.

Fair Value Measurements

Fair Value Measurements	6 Months Ended
	Jun. 30, 2024
Fair Value Disclosures [Abstract]
Fair Value Measurements	3. Fair Value Measurements The Company recognizes financial instruments in accordance with the authoritative guidance on fair value measurements and disclosures for financial assets and liabilities. This guidance defines fair value, establishes a framework for measuring fair value in accordance with GAAP, and expands disclosures about fair value measurements. The guidance also establishes a three-tier fair value hierarchy, which prioritizes the inputs used in measuring fair value. These tiers include Level 1, defined as observable inputs, such as quoted prices in active markets; Level 2, defined as inputs other than quoted prices in active markets that are either directly or indirectly observable; and Level 3, defined as unobservable inputs in which little or no market data exists, therefore, requiring an entity to develop its own assumptions. The Company’s financial instruments consist principally of cash and cash equivalents, money market funds, accounts receivable, accounts payable, interest rate swap hedges, and debt. The carrying value of cash and cash equivalents, accounts receivable, and accounts payable approximate fair value, primarily due to short maturities. Assets measured at fair value on a recurring basis are summarized below (in thousands): Fair Value Measurements at June 30, 2024 (unaudited) Level 1 Level 2 Level 3 Total Assets: Money market funds included in cash and cash equivalents $ 209,422 $ — $ — $ 209,422 Interest rate swaps — 14,933 — 14,933 Total $ 209,422 $ 14,933 $ — $ 224,355 Fair Value Measurements at December 31, 2023 Level 1 Level 2 Level 3 Total Assets: Money market funds included in cash and cash equivalents $ 211,661 $ — $ — $ 211,661 Interest rate swaps — 14,270 — 14,270 Total $ 211,661 $ 14,270 $ — $ 225,931 Money market funds included in cash and cash equivalents are highly-liquid investments and are measured at fair value using quoted market prices and active markets, therefore are categorized as Level 1. The fair value of the Company's interest rate swaps are measured at the end of each interim reporting period based on the then assessed fair value and adjusted if necessary. As the fair value measure is based on the market approach, they are categorized as Level 2. Debt

Goodwill and Other Intangible A

Goodwill and Other Intangible Assets	6 Months Ended
	Jun. 30, 2024
Goodwill and Intangible Assets Disclosure [Abstract]
Goodwill and Other Intangible Assets	4. Goodwill and Other Intangible Assets Changes in the Company’s goodwill balance for the six months ended June 30, 2024 are summarized in the table below (in thousands): Balance at December 31, 2023 $ 353,778 Impairment of goodwill (87,227) Foreign currency translation adjustment (2,387) Balance at June 30, 2024 $ 264,164 As a result of the decline of our stock price impacting our market capitalization during the quarter ended March 31, 2024, we performed a quantitative impairment evaluation, which resulted in a goodwill impairment of $87.2 million. Our quantitative goodwill impairment analysis applied two methodologies to estimate the Company’s fair value which were: a) a discounted cash flow method and b) a guideline public company method. The two methods indicated that the fair value of the Company was less than its carrying value. The discounted cash flow method required significant judgments, including estimation of future cash flows, which is dependent on internally developed forecasts, estimation of the long-term rate of growth for our business, and determination of our weighted average cost of capital. Under the guideline public company method, we estimated fair value based on a market multiple of revenues and earnings derived for comparable publicly traded companies with similar operating characteristics as the Company. We will continue to evaluate Goodwill for impairment and adjust as indicators arise. Intangible assets, net include the estimated acquisition-date fair values of customer relationships, marketing-related assets, and developed technology that the Company recorded as part of its business acquisitions. The following is a summary of the Company’s intangible assets, net (in thousands): Estimated Useful Gross Accumulated Net Carrying June 30, 2024: (unaudited) Customer relationships 1-10 $ 353,145 $ 220,490 $ 132,655 Trade name 1.5-10 9,446 7,696 1,750 Developed technology 4-9 86,722 68,395 18,327 Favorable Leases 6.3 271 107 164 Total intangible assets $ 449,584 $ 296,688 $ 152,896 Estimated Useful Gross Accumulated Net Carrying December 31, 2023: Customer relationships 1-10 $ 378,923 $ 222,436 $ 156,487 Trade name 1.5-10 10,012 7,862 2,150 Developed technology 4-9 94,103 70,582 23,521 Favorable Leases 6.3 280 89 191 Total intangible assets $ 483,318 $ 300,969 $ 182,349 Management recorded no impairments of intangible assets during the three and six months ended June 30, 2024 and June 30, 2023. The Company periodically reviews the estimated useful lives of its identifiable intangible assets, taking into consideration any events or circumstances that might result in either a diminished fair value or revised useful life. Total amortization expense was $13.5 million and $27.0 million during the three and six months ended June 30, 2024, respectively and $18.0 million and $36.1 million for the three and six months ended June 30, 2023, respectively.

Income Taxes

Income Taxes	6 Months Ended
	Jun. 30, 2024
Income Tax Disclosure [Abstract]
Income Taxes	5. Income Taxes The Company’s income tax benefit for the three and six months ended June 30, 2024 and June 30, 2023 reflects its estimate of the effective tax rates expected to be applicable for the full years, adjusted for any discrete events that are recorded in the period in which they occur. The estimates are re-evaluated each quarter based on the estimated tax expense for the full year. The income tax expense of $1.2 million and $0.7 million for the three and six months ended June 30, 2024, respectively, is largely comprised of foreign income taxes associated with our combined non-U.S. operations which is partially offset for the six months ended June 30, 2024 by the non-cash impact of deferred taxes related to the goodwill impairment recorded in the first quarter of 2024. The income tax benefit of $0.2 million and $1.7 million for the three and six months ended June 30, 2023, respectively, is primarily related to the non-cash impact of deferred taxes related to the goodwill impairment recorded during the first quarter of 2023. This tax benefit is offset by the foreign income taxes associated with our combined non-U.S. operations, changes in deferred tax liabilities associated with amortization of United States tax deductible goodwill, and state taxes in certain states in which the Company does not file on a consolidated basis or have net operating loss carryforwards. The Company historically incurred operating losses in the United States prior to 2021 and, given its cumulative losses and limited history of profits, has recorded a valuation allowance against its United States net deferred tax assets, exclusive of tax deductible goodwill, at June 30, 2024 and December 31, 2023, respectively. The company has also recorded valuation allowances in Germany, Australia and the United Kingdom to offset larger losses in those jurisdictions. The Company has reflected uncertain tax positions primarily within its long-term taxes payable and a portion within deferred tax assets for which the balance is immaterial at June 30, 2024. The Company and its subsidiaries file tax returns in the U.S. federal jurisdiction, several U.S. state jurisdictions and several foreign jurisdictions. The Company is no longer subject to U.S. federal income tax examinations for years ending before December 31, 2020 and is no longer subject to state and local or foreign income tax examinations by tax authorities for years ending before December 31, 2019, other than where cross-border transactions extend the statute of limitations. U.S. operating losses generated in years prior to 2020 remain open to adjustment until the statute of limitations closes for the tax year in which the net operating losses are utilized.

Debt

Debt	6 Months Ended
	Jun. 30, 2024
Debt Disclosure [Abstract]
Debt	6. Debt Long-term debt consisted of the following at June 30, 2024 and December 31, 2023 (in thousands): June 30, 2024 December 31, 2023 Senior secured loans (includes unamortized discount of $4,288 and $5,376 based on an imputed interest rate of 7.6% and 7.6%, at June 30, 2024 and December 31, 2023, respectively) $ 475,062 $ 476,674 Less current maturities (3,313) (3,172) Total long-term debt $ 471,749 $ 473,502 In August 2019, the Company entered into a credit agreement (the “Credit Facility”) which provides for (i) fully-drawn, 7 year, senior secured term loans (the “Term Loans”) maturing August 6, 2026 and (ii) a $60 million, 5 year, revolving credit facility (the “Revolver”) maturing August 6, 2024 that was undrawn as of June 30, 2024. The Term Loans are repayable on a quarterly basis beginning on December 31, 2019 by an amount equal to 0.25% (1.00% per annum) of the aggregate principal amount of such loan. Any amount remaining unpaid is due and payable in full on August 6, 2026. At the option of the Company, the Term Loans accrue interest at a per annum rate based on (i) the Base Rate (as defined below) plus a margin of 2.75% or (ii) the rate (not less than 0.00%) published by CME Group Benchmark Administration Limited (CBA), or as otherwise determined in accordance with the Credit Facility (based on a period equal to 1, 2, 3 or 6 months or, if available and agreed to by all relevant Lenders and the Agent, 12 months or such period of less than 1 month) plus a margin of 3.75%. The Base Rate for any day is a rate per annum equal to the greatest of (i) the prime rate in effect on such day, (ii) the Federal Funds Effective Rate (not less than 0.00%) in effect on such day plus ½ of 1.00%, and (iii) the Federal Funds Effective Rate for a one month interest period beginning on such day plus 1.00%. After giving effect to the interest rate swaps described below, $257.2 million of the Term Loans outstanding at June 30, 2024 has an effective annualized fixed interest rate of 5.4%, and the remaining principal outstanding at June 30, 2024 has a floating interest rate of 9.2% . Accrued interest is paid quarterly or, with respect to Term Loans that are accruing interest based on the Federal Funds Effective Rate, at the end of the applicable interest rate period. Loans under the Revolver are available up to $60 million. The Revolver provides a sub-facility whereby the Company may request letters of credit (the “Letters of Credit”) in an aggregate amount not to exceed, at any one time outstanding, $10 million for the Company. The aggregate amount of outstanding Letters of Credit are reserved against the credit availability under the Maximum Revolver Amount. As of June 30, 2024, the Company had no borrowings outstanding under the Revolver or related sub-facility. The Company incurs a 0.50% per annum unused line fee on the unborrowed balance of the Revolver which is paid quarterly. Loans under the Revolver may be borrowed, repaid and reborrowed until its maturity date, August 6, 2024, at which time any amounts borrowed under the Revolver must be repaid. Covenants The Credit Facility contains customary affirmative and negative covenants. The Credit Facility has no financial covenants as long as less than 35% of the Revolver is drawn as of the last day of any fiscal quarter. If 35% of the Revolver is drawn as of the last day of a given fiscal quarter the Company will be required to maintain a Total Leverage Ratio (the ratio of funded indebtedness as of such date less the amount of unrestricted cash and cash equivalents of the Company and its guarantors in an amount not to exceed $50.0 million, to adjusted EBITDA (calculated on a pro forma basis including giving effect to any acquisition)), measured on a quarter-end basis for each four consecutive fiscal quarters then ended, of not greater than 6.00 to 1.00. In addition, the Credit Facility contains customary events of default subject to customary cure periods. The occurrence of an event of default could result in the acceleration of the Term Loans and Revolver and a right by the agent and lenders to exercise remedies. At the election of the lenders, a default interest rate shall apply on all obligations during an event of default, at a rate per annum equal to 2.00% above the applicable interest rate. The Term Loans and Revolver are secured by substantially all of the Company's assets. As of June 30, 2024 the Company was in compliance with all covenants under the Credit Facility. Interest rate swaps In August 2019, the Company entered into floating-to-fixed interest rate swap agreements to limit exposure to interest rate risk related to our debt, effectively converting the entire balance of the Company's Term Loans from variable interest payments to fixed interest rate payments, based on an annualized fixed rate of 5.4%, for the 7-year term of debt. The interest rate associated with our undrawn $60 million Revolver remains floating. In August 2023, the Company sold a portion of the notional amount of its interest rate swap assets back to the counterparties for $20.5 million. At that time, a $20.5 million gain was recorded in accumulated other comprehensive income related to the notional amount sold. That gain is being released to interest expense, net as interest is accrued on the Company’s variable-rate debt over the remaining term of the Term Loans as a decrease to interest expense, net, the amortization of which totaled $1.5 million and $2.9 million for the three and six months ended June 30, 2024, respectively. Amounts reported in accumulated other comprehensive income related to the Company's derivatives are reclassified to interest expense, net as interest is accrued on the Company’s variable-rate debt. The impact of the Company’s derivative financial instruments on its condensed consolidated statements of comprehensive (loss) income for the three and six months ended June 30, 2024 and June 30, 2023 was as follows (in thousands): Three Months Ended June 30, Six Months Ended June 30, 2024 2023 2024 2023 Unrealized gain (loss) recognized in Other comprehensive income (loss) on interest rate swaps (956) $ 7,905 663 $ (249) Amounts reclassified from Accumulated other comprehensive income (loss) to interest expense, net (1,485) — (2,942) — Total Other comprehensive income (loss) on interest rate swaps $ (2,441) $ 7,905 $ (2,279) $ (249)

Net Loss Per Share

Net Loss Per Share	6 Months Ended
	Jun. 30, 2024
Earnings Per Share [Abstract]
Net Loss Per Share	7. Net Loss Per Share We compute loss per share of our common stock, par value $0.0001 per share (“Common Stock”) and Series A Preferred Stock , par value $0.0001 per share (“Series A Preferred Stock”) using the two-class method. The two-class method requires income available to common stockholders for the period to be allocated between Common Stock and participating securities based upon their respective rights to receive dividends as if all income for the period had been distributed. We consider our Series A Preferred Stock to be a participating security, as its holders are entitled to fully participate in any dividends or other distributions declared or paid on our Common Stock on an as-converted basis. The following table sets forth the computations of loss per share (in thousands, except share and per share amounts): Three Months Ended June 30, Six Months Ended June 30, 2024 2023 2024 2023 Numerator: Net Loss $ (11,439) $ (15,147) $ (107,569) $ (155,192) Preferred stock dividends and accretion (1,390) (1,329) (2,765) (2,644) Net loss attributable to common stockholders $ (12,829) $ (16,476) $ (110,334) $ (157,836) Denominator: Weighted–average common shares outstanding, basic and diluted 27,348,672 32,473,872 28,133,285 32,367,084 Net loss per common share, basic and diluted $ (0.47) $ (0.51) $ (3.92) $ (4.88) Due to the net losses for the three and six months ended June 30, 2024 and June 30, 2023, respectively, basic and diluted loss per share were the same. The Company uses the application of the if-converted method for calculating diluted earnings per share on our Series A Preferred Stock. The Company applies the treasury stock method for calculating diluted earnings per share on our stock options, restricted stock units and performance-based restricted stock units. Potential shares of common stock are excluded from the computation of diluted earnings per share when their effect would be antidilutive. Performance-based restricted stock units are considered dilutive when the related performance criteria have been met assuming the end of the reporting period represents the end of the performance period. All potential shares of common stock are antidilutive in periods of net loss. Potential shares of common stock not included in the computation of earnings per share because their effect would have been antidilutive or because the performance criterion was not met were as follows (in thousands): Contingently issuable shares associated with outstanding performance-based restricted stock units (each, a “PSU”) were not included in the basic earnings per share calculations for the periods presented, as the applicable vesting conditions had not been satisfied. June 30, 2024 2023 Stock options 122,530 152,683 Restricted stock units 2,716,299 2,242,054 Performance restricted stock units 350,000 193,750 Series A Preferred Stock on an if-converted basis (1) 7,140,482 6,827,998 Total anti–dilutive common share equivalents 10,329,311 9,416,485 (1) As of June 30, 2024 , the Series A Preferred Stock plus accumulated dividends totaled $125.0 million. The Series A Preferred Stock has a conversion price of $17.50 per share, as detailed in “ Note 9. Mezzanine Equity ”.

Commitments and Contingencies

Commitments and Contingencies	6 Months Ended
	Jun. 30, 2024
Commitments and Contingencies Disclosure [Abstract]
Commitments and Contingencies	8. Commitments and Contingencies Purchase Commitments The Company has purchase commitments related to hosting services, third-party technology used in the Company's solutions and for other services the Company purchases as part of normal operations. In certain cases these arrangements require a minimum annual purchase commitment. Litigation In the normal course of business, the Company is involved in various lawsuits and legal proceedings. The Company does not anticipate that any current or pending legal proceedings will have a material adverse effect on the Company's condensed consolidated balances sheets or condensed consolidated statements of operations.

Mezzanine Equity

Mezzanine Equity	6 Months Ended
	Jun. 30, 2024
Temporary Equity Disclosure [Abstract]
Mezzanine Equity	9. Mezzanine Equity Series A Convertible Preferred Stock On July 14, 2022, the Company entered into a Securities Purchase Agreement (the “Purchase Agreement”) with Ulysses Aggregator, LP (the “Purchaser”), an affiliate of HGGC, LLC, to issue and sell at closing 115,000 shares of Series A Preferred Stock of the Company, par value $0.0001 per share, at a price of $1,000 per share (the “Initial Liquidation Preference”) for an aggregate purchase price of $115.0 million (the “Investment”). On August 23, 2022 (the “Closing Date”), the closing of the Investment (the “Closing”) occurred, and the Series A Preferred Stock was issued to the Purchaser. In connection with the issuance of the Series A Preferred Stock, the Company incurred direct and incremental expenses of $4.6 million comprised of transaction fees, and financial advisory and legal expenses (the “Series A Preferred Stock Issuance Costs”), which reduced the carrying value of the Series A Preferred Stock. Contemporaneous with the Closing Date, the Company and the Purchaser entered into a Registration Rights Agreement (the “Registration Rights Agreement”) and the Company filed a Certificate of Designation (the “Certificate of Designation”) setting out the powers, designations, preferences, and other rights of the Series A Preferred Stock with the Secretary of State of the State of Delaware in connection with the Closing. Pursuant to the Registration Rights Agreement, the Purchaser has certain customary registration rights with respect to any shares of Series A Preferred Stock or the Common Stock of the Company issuable upon conversion of the Series A Preferred Stock, including rights with respect to the filing of a shelf registration statement, underwritten offering rights and piggy back rights. Dividend Provisions The Series A Preferred Stock ranks senior to the Company’s Common Stock with respect to payment of dividends and rights on the distribution of assets on any liquidation, dissolution or winding up of the affairs of the Company. The Series A Preferred Stock has an Initial Liquidation Preference of $1,000 per share, representing an aggregate Liquidation Preference (as defined below) of $1,000 upon issuance. Holders of the Series A Preferred Stock are entitled to the dividend at the rate of 4.5% per annum, within the first seven years after the Closing Date regardless of whether declared or assets are legally available for the payment. Such dividends shall accrue and compound quarterly in arrears from the date of issuance of the shares. The dividend rate will increase to 7.0% on the seven Liquidation Rights In the event of any Liquidation, holders of the Series A Preferred Stock are entitled to receive an amount per share equal to the greater of (1) the Initial Liquidation Preference per share plus any accrued or declared but unpaid dividends on such shares (the “Liquidation Preference”) or (2) the amount payable if the Series A Preferred Stock were converted into Common Stock. The Series A Preferred Stock will have distribution and liquidation rights senior to all other equity interests of the Company. As of June 30, 2024, the Liquidation Preference of the Series A Preferred Stock was $125.0 million. Optional Redemption On or after the 7th anniversary of the original issue date of the Series A Preferred Stock, the Company has the right to redeem any outstanding shares of the Series A Preferred Stock for a cash purchase price equal to 105% of the Liquidation Preference plus accrued and unpaid dividends as of the date of redemption. Deemed Liquidation Event Redemption Upon a fundamental change, holders of the Series A Preferred Stock have the right to require the Company to repurchase any or all of its Series A Preferred Stock for cash equal to the greater of (1) 105% of the Liquidation Preference plus the present value of the dividend payments the holders would have been entitled to through the fifth anniversary of the issue date and (2) the amount that such Preferred Stock would have been entitled to receive as if converted into common shares immediately prior to the fundamental change. A fundamental change (“Deemed Liquidation Event”) is defined as either the direct or indirect sale, lease, transfer, conveyance or other disposition of all or substantially all the properties or assets of the Company and its subsidiaries to any third party or the consummation of any transaction, the result of which is that any third party or group of third parties become the beneficial owner of more than 50% of the voting power of the Company. Voting Rights The Series A Preferred Stock will vote together with the common shares on all matters and not as a separate class (except as specifically provided in the Certificate of Designation or as otherwise required by law) on an as-converted basis. The holders of the Series A Preferred Stock will have the right to elect one member of the Board of Directors of the Company (the “Board of Directors”) for so long as holders of the Series A Preferred Stock own in the aggregate at least 5% of the shares of Common Stock on a fully diluted basis. In addition, the holders of the Series A Preferred Stock will have the right to elect one non-voting observer to the Board of Directors for so long as they hold at least 10% of the shares of Convertible Preferred Stock outstanding as of the date of the issue date. Conversion Feature The Series A Preferred Stock may be converted, at any time in whole or in part at the option of the holder into a number of shares of Common Stock equal to the quotient obtained by dividing the sum of the Liquidation Preference plus all accrued and unpaid dividends by the conversion price of $17.50 (the “Conversion Price”). The Conversion Price is subject to adjustment in the following events: • Stock splits and combinations • Tender offers or exchange offers • Distribution of rights, options, or warrants at a price per share that is less than the average of the last reported sale prices per share of Common Stock for the ten • Spin-offs and other distributed property • Issuance of equity-linked securities at a price per share less than the conversion price Anti-Dilution Provisions The Series A Preferred Stock has customary anti-dilution provisions for stock splits, stock dividends, mergers, sales of significant assets, and reorganization events and recapitalization transactions or similar events, and weighted average anti-dilution protection, subject to customary exceptions for issuances pursuant to current or future equity-based incentive plans or arrangements (including upon the exercise of employee stock options).

Stockholders' Equity

Stockholders' Equity	6 Months Ended
	Jun. 30, 2024
Equity [Abstract]
Stockholders' Equity	10. Stockholders' Equity Common Stock The common stock has a par value of 0.0001 per share. Each share of common stock is entitled to one vote at all meetings of stockholders. The number of authorized shares of common stock may be increased or decreased (but not below the number of shares thereof then outstanding) by the affirmative vote of the holders of shares of capital stock of the Company representing a majority of the votes represented by all outstanding shares of capital stock of the Company entitled to vote. The holders of common stock are also entitled to receive dividends, when, if and as declared by our board of directors, whenever funds are legally available therefore, subject to the priority rights of any outstanding preferred stock. Share repurchase program In September 2023, the Board of Directors authorized a stock repurchase program (the “Share Repurchase Plan”) in the aggregate amount of up to $25 million that allowed the Company to repurchase shares of its issued and outstanding Common Stock, from time to time in the open market or otherwise including pursuant to a Rule 10b5-1 trading plan and in compliance with Rule10b-18 under the Exchange Act so long as the aggregate purchase price paid for such transactions does not exceed $25 million for all such purchases. The Share Repurchase Plan expired in May 2024 when the Company had repurchased all shares authorized for repurchase. 6,453,805 total shares were repurchased under the Share Repurchase Plan from September 2023 through its completion in May 2024. In fiscal year 2024, the Company’s net stock repurchases are subject to a 1 percent excise tax under the Inflation Reduction Act. The excise tax is included as a reduction to accumulated deficit in the condensed consolidated statements of stockholders equity. Total accrued excise tax of $0.2 million is included in total cost of shares repurchased, excluded from average cost per share and excluded from total cash paid during the three months ended June 30, 2024 as amounts were unpaid at period end. During the three and six months ended June 30, 2024, the Company repurchased and subsequently retired 966,051 and 3,208,705 shares of Common Stock, respectively, for a total of $2.8 million and $11.0 million, respectively, cash paid under the Share Repurchase Plan. As of June 30, 2024, the Share Repurchase Plan was complete and no further amounts are available for share repurchases. Tax Benefit Preservation Plan and Preferred Stock Purchase Rights The preferred stock purchase rights (“the 2023 Rights”), as described in the Tax Benefit Preservation Plan dated as of May 2, 2023, by and between Upland Software, Inc. and Broadridge Corporate Issuer Solutions, LLC, as Rights Agent, (the “2023 Tax Benefit Preservation Plan”), expired on May 1, 2024, pursuant to the terms of the 2023 Tax Benefit Preservation Plan. The Company filed a Form 15-12G on May 29, 2024 to terminate the registration of the 2023 Rights. On June 5, 2024 at the Company’s annual meeting of stockholders, the Company’s stockholders approved the 2024 Tax Benefit Preservation Plan between the Company and Broadridge Corporate Issuer Solutions, LLC, as Rights Agent (the “2024 Tax Benefit Preservation Plan”), which had previously been approved by the Company’s Board of Directors on April 12, 2024, subject to stockholder approval. Also on April 12, 2024, the Board of Directors declared, subject to approval by the stockholders at the annual meeting, a dividend of one preferred stock purchase right (a “2024 Right”) for each outstanding share of Common Stock payable as of June 15, 2024. 27,030,605 2024 Rights were issued to the holders of record of shares of Common Stock. The description and terms of the 2024 Rights are set forth in the 2024 Tax Benefit Preservation Plan. The Company filed a Form 8-A to register the 2024 Rights on June 5, 2024. By adopting the 2024 Tax Benefit Preservation Plan, the Board of Directors is seeking to protect the Company’s ability to use its net operating loss carryforwards (“NOLs”) and other tax attributes to offset potential future income tax liabilities. The Company’s ability to use such NOLs and other tax attributes would be substantially limited if the Company experiences an “ownership change,” as defined in Section 382 of the Internal Revenue Code (the “Code”). Generally, an “ownership change” occurs if the percentage of the Company’s stock owned by one or more “five percent stockholders” increases by more than fifty percentage points over the lowest percentage of stock owned by such stockholders at any time during the prior three-year period or, if sooner, since the last “ownership change” experienced by the Company. The 2024 Tax Benefit Preservation Plan is intended to make it more difficult for the Company to undergo an ownership change by deterring any person from acquiring 4.9% or more of the outstanding shares of stock without the approval of the Board of Directors. The Board of Directors believes it is in the best interest of the Company and its stockholders to reduce the likelihood of an ownership change, which could harm the Company’s future operating results by effectively increasing the Company future tax liabilities. The 2024 Rights trade with, and are inseparable from, the Common Stock, and the record holders of shares of Common Stock are the record holders of the 2024 Rights. The 2024 Rights are evidenced only by certificates (or, in the case of uncertificated shares, by notations in the book-entry account system) that represent shares of Common Stock. 2024 Rights will also be issued in respect of any shares of Common Stock that shall become outstanding after the Record Date (including upon conversion of any shares of Series A Preferred Stock of the Company) and, subject to certain exceptions specified in the 2024 Tax Benefit Preservation Plan, prior to the earlier of the Distribution Date (as defined below) and the Expiration Date (as defined below). The 2024 Rights are not exercisable until the Distribution Date. After the Distribution Date, each 2024 Right will be exercisable to purchase from the Company one one-thousandth of a share of Series B Junior Participating Preferred Stock, par value $0.0001 per share, of the Company (the “Series B Preferred”), at a purchase price of $15.25 per one one-thousandth of a share of Series B Preferred (the “Purchase Price”), subject to adjustment as provided in the 2024 Tax Benefit Preservation Plan. The “Distribution Date” is the earlier of (i) the close of business on the tenth day after the public announcement that a person or group has become an Acquiring Person (as defined below) or that discloses information which reveals the existence of an Acquiring Person or such earlier date as a majority of the Board shall become aware of the existence of an Acquiring Person (the date described in this clause (i), the “Stock Acquisition Date”) and (ii) the close of business on the tenth business day (or such later date as the Board of Directors shall determine prior to such time as any person or group becomes an Acquiring Person) after the date that a tender or exchange offer by any person is commenced, the consummation of which would result in such person becoming an Acquiring Person. A person or group becomes an “Acquiring Person” upon acquiring beneficial ownership of 4.9% or more of the outstanding shares of Common Stock, except in certain situations specified in the 2024 Tax Benefit Preservation Plan. The 2024 Rights will expire on the earliest of (a) the close of business on June 4, 2027, (b) the time at which the Rights are redeemed or exchanged pursuant to the 2024 Tax Benefit Preservation Plan, or (c) the time at which the Rights are exchanged as provided in the 2024 Tax Benefit Preservation Plan, or (d) the time at which the Board of Directors determines that the Tax Benefits are utilized in all material respects or that an ownership change under Section 382 of the Code would not adversely impact in any material respect the time period in which the Company could use the Tax Benefits, or materially impair the amount of the Tax Benefits that could be used by the Company in any particular time period, for applicable tax purposes (such earliest date, the “Expiration Date”). Until a Right is exercised or exchanged, the holder thereof, as such, will have no rights as a stockholder of the Company by virtue of holding such Right, including, without limitation, the right to vote and to receive dividends. The Board of Directors may adjust the Purchase Price, the number of shares of Series B Preferred issuable and the number of outstanding 2024 Rights to prevent dilution that may occur from a stock dividend, a stock split, a reclassification of the Series B Preferred or Common Stock or certain other specified transactions. No adjustments to the Purchase Price of less than 1% are required to be made. In connection with the adoption of the 2023 Tax Benefit Preservation Plan, the Board of Directors approved a Certificate of Designations of the Series B Junior Participating Preferred Stock (the “Certificate of Designations”). The Certificate of Designations was filed with the Secretary of State of the State of Delaware on May 2, 2023. Each one one-thousandth of a share of Series B Preferred, if issued: • Will not be redeemable. • Will entitle holders to quarterly dividend payments of $0.001 per one one-thousandth of a share of Series B Preferred, or an amount equal to the dividend paid on one share of Common Stock, whichever is greater. • Will entitle holders upon liquidation either to receive $0.001 per one one-thousandth of a share of Series B Preferred, or an amount equal to the payment made on one share of Common Stock, whichever is greater. • Will have the same voting power as one share of Common Stock. • If shares of Common Stock are exchanged as a result of a merger, consolidation, or a similar transaction, will entitle holders to a per share payment equal to the payment made on one share of Common Stock. Accumulated Other Comprehensive Income (Loss) Comprehensive income consists of two elements, net loss and other comprehensive income (loss). Other comprehensive income (loss) items are recorded in the stockholders’ equity section of our condensed consolidated balance sheets and are excluded from net loss. Our other comprehensive income consists primarily of foreign currency translation adjustments for subsidiaries with functional currencies other than the U.S. dollar, unrealized translation losses on intercompany loans with foreign subsidiaries, and unrealized gains on interest rate swaps. The following table shows the components of accumulated other comprehensive income (loss), net of income taxes, (“AOCI”) in the stockholders’ equity section of our condensed consolidated balance sheets at the dates indicated (in thousands): June 30, 2024 December 31, 2023 Foreign currency translation adjustment $ (22,766) $ (19,947) Unrealized translation loss on intercompany loans with foreign subsidiaries, net of taxes (5,000) (3,330) Unrealized gain on interest rate swaps 14,933 14,270 Realized gain on interest rate swap sale, net of amounts reclassified into interest expense, net 12,233 15,175 Total accumulated other comprehensive income (loss) $ (600) $ 6,168 The Company has intercompany loans that were used to fund the acquisitions of foreign subsidiaries. Due to the long-term nature of the loans, the unrealized translation gains (losses) resulting from re-measurement are recognized as a component of AOCI. The unrealized translation gains (losses) on intercompany loans with foreign subsidiaries as of June 30, 2024 is net of income tax expense of $3.1 million. The tax benefit related to unrealized translation gains (losses) on intercompany loans for the three and six months ended June 30, 2024 was $0.1 million and $0.2 million, respectively. The tax provision related to unrealized translation gains (losses) on intercompany loans for the three and six months ended June 30, 2023 was $0.5 million and $1.0 million, respectively. The income tax expense/benefit allocated to each component of other comprehensive income for all other periods and components is not material. The Company reclassifies taxes from AOCI to earnings as the items to which the tax effects relate are similarly reclassified. The functional currency of our foreign subsidiaries are the local currencies. Results of operations for foreign subsidiaries are translated into United States dollars (“USD”) using the average exchange rates on a monthly basis during the year. The assets and liabilities of those subsidiaries are translated into USD using the exchange rates in effect at the balance sheet date. The related translation adjustments are recorded in a separate component of stockholders' equity in AOCI. Stock-Based Compensation The Company’s stock-based compensation generally includes awards of restricted stock units (“RSUs”) and performance-based restricted stock units (“PSUs”). Key employees, officers and directors of the Company and its consultants or advisors are eligible to receive awards. On June 5, 2024, the Company’s stockholders approved the Upland Software, Inc. 2024 Omnibus Incentive Plan (the “2024 Equity Plan”). No further awards will be made under the Upland Software, Inc. 2014 Equity Incentive Plan (the “Prior Plan”) or the Amended and Restated Upland Software, Inc. 2010 Stock Option Plan (the “2010 Plan”). As of June 30, 2024, there were 122,530 outstanding options that were previously granted under the 2010 Plan and the Prior Plan. The Company no longer grants stock options; however if the outstanding options were to be forfeited or otherwise canceled without the issuance of shares, the shares underlying those stock options will become available for issuance under the 2024 Equity Plan. As of June 30, 2024, there were 3,066,299 outstanding RSU and PSU awards under the Prior Plan that will remain outstanding and subject to the terms of the Prior Plan and the respective award agreements, until the vesting, expiration or lapse of such awards in accordance with their terms. Any shares covered by awards granted under the Prior Plan will become available for issuance under the 2024 Equity Plan if the award (or a portion of such award) is forfeited, canceled or expires without the issuance of shares. The following table summarizes PSU and RSU activity during the six months ended June 30, 2024: Number of Units Weighted-Average Grant Date Fair Value Unvested restricted units outstanding as of December 31, 2023 1,858,847 $ 9.76 Granted 2,122,687 4.13 Vested (791,414) 8.89 Forfeited (123,821) 10.17 Unvested restricted units outstanding as of June 30, 2024 3,066,299 $ 6.07 The PSU and RSU activity table above includes 100,000 PSUs granted in 2023 and 250,000 PSUs granted in 2024 based on a 100% target payout. Compensation cost related to awards is based on the fair market value at the time of the grant. The fair value of the RSUs is determined based on the grant date fair value of the award. Compensation expense for RSUs is recognized over the required service period of the grant. The PSUs vest upon the achievement of specified market performance thresholds. The PSUs have a vesting condition that is tied to the Company’s total shareholder return based on the Company’s stock performance up to a maximum of 200% and 300%, depending on the specified performance condition and the level of achievement obtained, for the 2023 PSUs and 2024 PSUs, respectively. The fair value of PSUs is determined using the Monte Carlo simulation model. Compensation expense for PSUs is recognized over the requisite service period and is not subject to adjustment regardless of whether the PSUs meet the performance metric. The range of significant assumptions used in the Monte Carlo simulation model for the PSUs granted during the six months ended June 30, 2024 was as follows: Expected volatility 74.6% - 62.06% Risk-free interest rate 4.4% - 4.0% Remaining performance period (in years) 2.73 - 2.73 Dividend yield — The Company recognizes stock-based compensation expense from all awards in the following expense categories included in our condensed consolidated statements of income (in thousands): Three Months Ended June 30, Six Months Ended June 30, 2024 2023 2024 2023 Cost of revenue $ 199 $ 301 $ 385 $ 604 Research and development 638 648 1,244 1,303 Sales and marketing 362 558 759 1,134 General and administrative 3,934 4,863 6,267 9,791 Total $ 5,133 $ 6,370 $ 8,655 $ 12,832

Revenue Recognition

Revenue Recognition	6 Months Ended
	Jun. 30, 2024
Revenue from Contract with Customer [Abstract]
Revenue Recognition	11. Revenue Recognition Revenue Recognition Policy Revenue is recognized when control of the promised goods or services is transferred to the Company's customers, in an amount that reflects the consideration the Company expects to be entitled to in exchange for those goods or services over the term of the agreement, generally when made available to the customers. We enter into contracts that can include various combinations of products and services, which are generally capable of being distinct and accounted for as separate performance obligations. Revenue is recognized net of sales credits and allowances. Revenue is recognized net of any taxes collected from customers, which are subsequently remitted to governmental authorities. Revenue is recognized based on the following five step model in accordance with ASC 606, Revenue from Contracts with Customers : • Identification of the contract with a customer • Identification of the performance obligations in the contract • Determination of the transaction price • Allocation of the transaction price to the performance obligations in the contract • Recognition of revenue when, or as, the Company satisfies a performance obligation Performance obligations under our contracts consist of subscription and support, perpetual licenses, and professional services revenues within a single operating segment. Subscription and Support Revenue The Company's software solutions are available for use as hosted application arrangements under subscription fee agreements without licensing perpetual rights to the software. Subscription fees from these applications are recognized over time on a ratable basis over the customer agreement term beginning on the date the Company's solution is made available to the customer. As our customers have access to use our solutions over the term of the contract agreement we believe this method of revenue recognition provides a faithful depiction of the transfer of services provided. Our subscription contracts are generally 1 to 3 years in length. Amounts that have been invoiced are recorded in accounts receivable and deferred revenue or subscription and support revenue, depending on whether the revenue recognition criteria have been met. Additional fees for monthly usage above the levels included in the standard subscription fee are recognized as subscription and support revenue at the end of each month and are invoiced concurrently. Subscription and support revenue includes revenue related to the Company’s digital engagement application which provides short code connectivity for its two-way short message service (“SMS”) programs and campaigns. As discussed further in the “Principal vs. Agent Considerations” section below, the Company recognizes revenue related to these messaging-related subscription contracts on a gross basis. Perpetual License Revenue The Company also records revenue from the sales of proprietary software products under perpetual licenses. Revenue from distinct on-premises licenses is recognized upfront at the point in time when the software is made available to the customer. The majority of the Company’s products do not require significant customization. Professional Services Revenue Professional services provided with subscription and support licenses and perpetual licenses consist of implementation fees, data extraction, configuration, and training. The Company’s implementation and configuration services do not involve significant customization of the software and are not considered essential to the functionality. Revenue from professional services are recognized over time as such services are performed. Revenue for fixed price services are generally recognized over time applying input methods to estimate progress to completion. Revenue for consumption-based services are generally recognized as the services are performed. Performance Obligations and Standalone Selling Price A performance obligation is a promise in a contract to transfer a distinct good or service to the customer and is the unit of accounting. The Company has contracts with customers that often include multiple performance obligations, usually including professional services sold with either individual or multiple subscriptions or perpetual licenses. For these contracts, the Company records individual performance obligations separately if they are distinct by allocating the contract's total transaction price to each performance obligation in an amount based on the relative standalone selling price (“SSP”), of each distinct good or service in the contract. We only include estimated amounts of variable consideration in the transaction price to the extent it is probable that a significant reversal of cumulative revenue recognized will not occur when the uncertainty associated with the variable consideration is resolved. A contract's transaction price is allocated to each distinct performance obligation and is recognized as revenue when, or as, the performance obligation is satisfied. We determine the SSP based on our overall pricing objectives, taking into consideration market conditions and other factors, including the value of our contracts, historical standalone sales, customer demographics, geographic locations, and the number and types of users within our contracts. Principal vs. Agent Considerations The Company evaluates whether it is the principal (i.e., report revenues on a gross basis) or agent (i.e., report revenues on a net basis) for vendor reseller agreements and messaging-related subscription agreements. Where the Company is the principal, it first obtains control of the inputs to the specific good or service and directs their use to create the combined output. The Company's control is evidenced by its involvement in the integration of the good or service on its platform before it is transferred to its customers, and is further supported by the Company being primarily responsible to its customers and having a level of discretion in establishing pricing. While none of the factors individually are considered presumptive or determinative, in reaching conclusions on gross versus net revenue recognition, the Company places the most weight on the analysis of whether or not it is the primary obligor in the arrangement. Generally, the Company reports revenue from vendor reseller agreements on a gross basis, meaning the amounts billed to customers are recorded as revenue, and expenses incurred are recorded as cost of revenue. As the Company is primarily obligated in its messaging-related subscription contracts, has latitude in establishing prices associated with its messaging program management services, is responsible for fulfillment of the transaction, and has credit risk, we have concluded it is appropriate to record revenue on a gross basis with related pass-through telecom messaging costs incurred from third parties recorded as cost of revenue. Revenue provided from agreements in which the Company is an agent are immaterial. Contract Balances The timing of revenue recognition, billings and cash collections can result in billed accounts receivable, unbilled receivables, and deferred revenue. Billings scheduled to occur after the performance obligation has been satisfied and revenue recognition has occurred result in unbilled receivables, which are expected to be billed during the succeeding twelve-month period and are recorded in Unbilled receivables in our condensed consolidated balance sheets. A contract liability results when we receive prepayments or deposits from customers in advance for implementation, maintenance and other services, as well as subscription fees. Customer prepayments are generally applied against invoices issued to customers when services are performed and billed. We recognize contract liabilities as revenue upon satisfaction of the underlying performance obligations. Contract liabilities that are expected to be recognized as revenue during the succeeding twelve-month period are recorded in Deferred revenue and the remaining portion is recorded in Deferred revenue noncurrent on the accompanying condensed consolidated balance sheets at the end of each reporting period. Deferred revenue primarily consists of amounts that have been billed to or received from customers in advance of revenue recognition and prepayments received from customers in advance for maintenance and other services, as well as initial subscription fees. We recognize deferred revenue as revenue when the services are performed, and the corresponding revenue recognition criteria are met. Customer prepayments are generally applied against invoices issued to customers when services are performed and billed. Our payment terms vary by the type and location of our customer and the products or services offered. The term between invoicing and when payment is due is not significant. For certain products or services and customer types, we require payment before the products or services are delivered to the customer. Unbilled Receivables Unbilled receivables represent amounts for which the Company has recognized revenue, pursuant to its revenue recognition policy, for software licenses already delivered and professional services already performed, but invoiced in arrears and for which the Company believes it has an unconditional right to payment. As of June 30, 2024 and December 31, 2023, unbilled receivables were $3.5 million and $2.7 million, respectively. Deferred Commissions Sales commissions earned by our sales force, and related payroll taxes, are considered incremental and recoverable costs of obtaining a contract with a customer. Deferred commissions and other costs for new customer contracts are capitalized upon contract signing and amortized on a systematic basis that is consistent with the transfer of goods and services over the expected life of the customer relationships, which has been determined to be approximately 6 years. The expected life of our customer relationships is based on historical data and management estimates, including estimated renewal terms and the useful life of the associated underlying technology. Commissions paid on renewal contracts are not commensurate with commissions paid on new customer contracts, as such, deferred commissions related to renewals are capitalized and amortized over the estimated average contractual renewal term of 18 months. We utilize the 'portfolio approach' practical expedient permitted under ASC 606-10-10-4, which allows entities to apply the guidance to a portfolio of contracts with similar characteristics as the effects on the financial statements of this approach would not differ materially from applying the guidance to individual contracts. The portion of capitalized costs expected to be amortized during the succeeding twelve-month period is recorded in current assets as deferred commissions, current, and the remainder is recorded in long-term assets as deferred commissions, net of current portion. Amortization expense is included in sales and marketing expenses in the accompanying condensed consolidated statements of operations. Deferred commissions are reviewed for impairment whenever events or circumstances indicate their carrying value may not be recoverable consistent with the Company's long-lived assets policy. No indicators of impairment were identified during the six months ended June 30, 2024. Amortization of deferred commissions in excess of commissions capitalized for the three and six months ended June 30, 2024 was $0.3 million and $1.0 million, respectively. Deferred Revenue Deferred revenue represents either customer advance payments or billings for which the aforementioned revenue recognition criteria have not yet been met. Deferred revenue is mainly unearned revenue related to subscription services and support services. During the six months ended June 30, 2024, we recognized $72.7 million and $1.8 million of subscription services and professional services revenue, respectively, that was included in the deferred revenue balances at the beginning of the period. Remaining Performance Obligations As of June 30, 2024, approximately $252.7 million of revenue is expected to be recognized from remaining performance obligations. We expect to recognize revenue on approximately 69% of these remaining performance obligations over the next 12 months, with the balance recognized thereafter. Disaggregated Revenue The Company disaggregates revenue from contracts with customers by geography and revenue generating activity, as it believes it best depicts how the nature, amount, timing and uncertainty of revenue and cash flows are affected by economic factors. Revenue by geography is based on the ship-to address of the customer, which is intended to approximate where the customers' users are located. The ship-to country is generally the same as the billing country. The Company has operations primarily in the United States, United Kingdom and Canada. Information about these operations is presented below (in thousands): Three Months Ended June 30, Six Months Ended June 30, 2024 2023 2024 2023 Revenues: Subscription and support: United States $ 47,342 $ 50,162 $ 95,066 $ 102,403 United Kingdom 8,397 9,160 17,472 18,835 Canada 3,217 3,441 6,545 6,932 Other International 6,548 7,731 13,499 15,238 Total subscription and support revenue 65,504 70,494 132,582 143,408 Perpetual license: United States 879 721 1,570 1,377 United Kingdom 56 69 155 292 Canada 93 14 152 56 Other International 702 448 1,323 1,098 Total perpetual license revenue 1,730 1,252 3,200 2,823 Professional services: United States 1,212 1,557 2,445 3,155 United Kingdom 243 452 514 710 Canada 146 230 334 459 Other International 504 512 1,000 998 Total professional service revenue 2,105 2,751 4,293 5,322 Total revenue $ 69,339 $ 74,497 $ 140,075 $ 151,553

Pay vs Performance Disclosure

Pay vs Performance Disclosure - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2024	Jun. 30, 2023	Jun. 30, 2024	Jun. 30, 2023
Pay vs Performance Disclosure
Net loss	$ (11,439)	$ (15,147)	$ (107,569)	$ (155,192)

Insider Trading Arrangements

Insider Trading Arrangements	3 Months Ended
	Jun. 30, 2024
Trading Arrangements, by Individual
Rule 10b5-1 Arrangement Adopted	false
Non-Rule 10b5-1 Arrangement Adopted	false
Rule 10b5-1 Arrangement Terminated	false
Non-Rule 10b5-1 Arrangement Terminated	false

Basis of Presentation and Sum_2

Basis of Presentation and Summary of Significant Accounting Policies (Policies)	6 Months Ended
	Jun. 30, 2024
Accounting Policies [Abstract]
Basis of Presentation	Basis of Presentation These condensed consolidated financial statements have been prepared in conformity with accounting principles generally accepted in the United States (“GAAP”). The condensed consolidated financial statements include the accounts of Upland Software, Inc. and its wholly owned subsidiaries (collectively referred to as “Upland”, the “Company”, “we”, “us” or “our”). All intercompany accounts and transactions have been eliminated in consolidation. No material changes have been made to the Company’s significant accounting policies disclosed in Note 2, Basis of Presentation and Summary of Significant Accounting Policies , in our Annual Report. The accompanying unaudited interim condensed consolidated financial statements have been prepared pursuant to the rules and regulations of the Securities and Exchange Commission (the “SEC”) for interim financial reporting. In the opinion of management of the Company, the unaudited interim condensed consolidated financial statements have been prepared on the same basis as the audited consolidated financial statements, in all material respects, and include all adjustments of a normal recurring nature necessary for a fair presentation. The results of operations for the six months ended June 30, 2024 are not necessarily indicative of the results to be expected for the year ending December 31, 2024 or for any other period. The financial statements should be read in conjunction with the consolidated financial statements and notes thereto included in the Company’s 2023 Annual Report on Form 10-K filed with the SEC on February 22, 2024.
Use of Estimates	Use of Estimates The preparation of the accompanying condensed consolidated financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities, disclosure of contingent assets and liabilities at the date of the condensed consolidated financial statements, and the reported amounts of revenues and expenses. Significant items subject to such estimates include those related to revenue recognition, deferred commissions, allowance for credit losses, stock-based compensation, contingent consideration, acquired intangible assets, impairment of goodwill, intangibles and long-lived assets, the useful lives of intangible assets and property and equipment, the fair value of the Company’s interest rate swaps and income taxes. In accordance with GAAP, management bases its estimates on historical experience and on various other assumptions that management believes are reasonable under the circumstances. Management regularly evaluates its estimates and assumptions using historical experience and other factors; however, actual results could differ from those estimates.
Concentrations of Credit Risk and Significant Customers	Concentrations of Credit Risk and Significant Customers Financial instruments that potentially subject the Company to credit risk consist of cash and cash equivalents, accounts receivable and the Company’s interest rate swap hedges. The Company’s cash and cash equivalents are placed with high quality financial institutions, which, at times, may exceed federally insured limits. The Company has not experienced any losses in these accounts, and the Company does not believe it is exposed to any significant credit risk related to cash and cash equivalents. The Company provides credit, in the normal course of business, to a number of its customers and generally does not require collateral. To manage accounts receivable credit risk, the Company performs periodic credit evaluations of its customers and maintains current expected credit losses which considers such factors as historical loss information, geographic location of customers, current market conditions, and reasonable and supportable forecasts.
Recent Accounting Pronouncements	Recent Accounting Pronouncements Recently issued accounting pronouncements - Not Adopted In November 2023, the FASB issued ASU 2023-07, Segment Reporting (Topic 280): Improvements to Reportable Segment Disclosures , which requires public entities to disclose information about their reportable segments' significant expenses and other segment items on an interim and annual basis. Public entities with a single reportable segment are required to apply the disclosure requirements in ASU 2023-07, as well as all existing segment disclosures and reconciliation requirements in ASC 280 on an interim and annual basis. ASU 2023-07 is effective for fiscal years beginning after December 15, 2023, and for interim periods within fiscal years beginning after December 15, 2024, with early adoption permitted. ASU 2023-07 should be applied on a retrospective basis. The Company is currently evaluating the impact of adopting ASU 2023-07 on its disclosures. In December 2023, the FASB issued ASU 2023-09, Income Taxes (Topic 740): Improvements to Income Tax Disclosures , which requires public entities, on an annual basis, to provide disclosure of specific categories in the rate reconciliation, as well as disclosure of income taxes paid disaggregated by jurisdiction. ASU 2023-09 is effective for fiscal years beginning after December 15, 2024, with early adoption permitted. ASU 2023-09 should be applied on a prospective basis, and retrospective application is permitted. The Company is currently evaluating the impact of adopting ASU 2023-09 on its disclosures.
Fair Value Measurements	The Company recognizes financial instruments in accordance with the authoritative guidance on fair value measurements and disclosures for financial assets and liabilities. This guidance defines fair value, establishes a framework for measuring fair value in accordance with GAAP, and expands disclosures about fair value measurements. The guidance also establishes a three-tier fair value hierarchy, which prioritizes the inputs used in measuring fair value. These tiers include Level 1, defined as observable inputs, such as quoted prices in active markets; Level 2, defined as inputs other than quoted prices in active markets that are either directly or indirectly observable; and Level 3, defined as unobservable inputs in which little or no market data exists, therefore, requiring an entity to develop its own assumptions.
Revenue Recognition Policy	Revenue Recognition Policy Revenue is recognized when control of the promised goods or services is transferred to the Company's customers, in an amount that reflects the consideration the Company expects to be entitled to in exchange for those goods or services over the term of the agreement, generally when made available to the customers. We enter into contracts that can include various combinations of products and services, which are generally capable of being distinct and accounted for as separate performance obligations. Revenue is recognized net of sales credits and allowances. Revenue is recognized net of any taxes collected from customers, which are subsequently remitted to governmental authorities. Revenue is recognized based on the following five step model in accordance with ASC 606, Revenue from Contracts with Customers : • Identification of the contract with a customer • Identification of the performance obligations in the contract • Determination of the transaction price • Allocation of the transaction price to the performance obligations in the contract • Recognition of revenue when, or as, the Company satisfies a performance obligation Performance obligations under our contracts consist of subscription and support, perpetual licenses, and professional services revenues within a single operating segment. Subscription and Support Revenue The Company's software solutions are available for use as hosted application arrangements under subscription fee agreements without licensing perpetual rights to the software. Subscription fees from these applications are recognized over time on a ratable basis over the customer agreement term beginning on the date the Company's solution is made available to the customer. As our customers have access to use our solutions over the term of the contract agreement we believe this method of revenue recognition provides a faithful depiction of the transfer of services provided. Our subscription contracts are generally 1 to 3 years in length. Amounts that have been invoiced are recorded in accounts receivable and deferred revenue or subscription and support revenue, depending on whether the revenue recognition criteria have been met. Additional fees for monthly usage above the levels included in the standard subscription fee are recognized as subscription and support revenue at the end of each month and are invoiced concurrently. Subscription and support revenue includes revenue related to the Company’s digital engagement application which provides short code connectivity for its two-way short message service (“SMS”) programs and campaigns. As discussed further in the “Principal vs. Agent Considerations” section below, the Company recognizes revenue related to these messaging-related subscription contracts on a gross basis. Perpetual License Revenue The Company also records revenue from the sales of proprietary software products under perpetual licenses. Revenue from distinct on-premises licenses is recognized upfront at the point in time when the software is made available to the customer. The majority of the Company’s products do not require significant customization. Professional Services Revenue Professional services provided with subscription and support licenses and perpetual licenses consist of implementation fees, data extraction, configuration, and training. The Company’s implementation and configuration services do not involve significant customization of the software and are not considered essential to the functionality. Revenue from professional services are recognized over time as such services are performed. Revenue for fixed price services are generally recognized over time applying input methods to estimate progress to completion. Revenue for consumption-based services are generally recognized as the services are performed. Performance Obligations and Standalone Selling Price A performance obligation is a promise in a contract to transfer a distinct good or service to the customer and is the unit of accounting. The Company has contracts with customers that often include multiple performance obligations, usually including professional services sold with either individual or multiple subscriptions or perpetual licenses. For these contracts, the Company records individual performance obligations separately if they are distinct by allocating the contract's total transaction price to each performance obligation in an amount based on the relative standalone selling price (“SSP”), of each distinct good or service in the contract. We only include estimated amounts of variable consideration in the transaction price to the extent it is probable that a significant reversal of cumulative revenue recognized will not occur when the uncertainty associated with the variable consideration is resolved. A contract's transaction price is allocated to each distinct performance obligation and is recognized as revenue when, or as, the performance obligation is satisfied. We determine the SSP based on our overall pricing objectives, taking into consideration market conditions and other factors, including the value of our contracts, historical standalone sales, customer demographics, geographic locations, and the number and types of users within our contracts. Principal vs. Agent Considerations The Company evaluates whether it is the principal (i.e., report revenues on a gross basis) or agent (i.e., report revenues on a net basis) for vendor reseller agreements and messaging-related subscription agreements. Where the Company is the principal, it first obtains control of the inputs to the specific good or service and directs their use to create the combined output. The Company's control is evidenced by its involvement in the integration of the good or service on its platform before it is transferred to its customers, and is further supported by the Company being primarily responsible to its customers and having a level of discretion in establishing pricing. While none of the factors individually are considered presumptive or determinative, in reaching conclusions on gross versus net revenue recognition, the Company places the most weight on the analysis of whether or not it is the primary obligor in the arrangement. Generally, the Company reports revenue from vendor reseller agreements on a gross basis, meaning the amounts billed to customers are recorded as revenue, and expenses incurred are recorded as cost of revenue. As the Company is primarily obligated in its messaging-related subscription contracts, has latitude in establishing prices associated with its messaging program management services, is responsible for fulfillment of the transaction, and has credit risk, we have concluded it is appropriate to record revenue on a gross basis with related pass-through telecom messaging costs incurred from third parties recorded as cost of revenue. Revenue provided from agreements in which the Company is an agent are immaterial. Contract Balances The timing of revenue recognition, billings and cash collections can result in billed accounts receivable, unbilled receivables, and deferred revenue. Billings scheduled to occur after the performance obligation has been satisfied and revenue recognition has occurred result in unbilled receivables, which are expected to be billed during the succeeding twelve-month period and are recorded in Unbilled receivables in our condensed consolidated balance sheets. A contract liability results when we receive prepayments or deposits from customers in advance for implementation, maintenance and other services, as well as subscription fees. Customer prepayments are generally applied against invoices issued to customers when services are performed and billed. We recognize contract liabilities as revenue upon satisfaction of the underlying performance obligations. Contract liabilities that are expected to be recognized as revenue during the succeeding twelve-month period are recorded in Deferred revenue and the remaining portion is recorded in Deferred revenue noncurrent on the accompanying condensed consolidated balance sheets at the end of each reporting period. Deferred revenue primarily consists of amounts that have been billed to or received from customers in advance of revenue recognition and prepayments received from customers in advance for maintenance and other services, as well as initial subscription fees. We recognize deferred revenue as revenue when the services are performed, and the corresponding revenue recognition criteria are met. Customer prepayments are generally applied against invoices issued to customers when services are performed and billed. Our payment terms vary by the type and location of our customer and the products or services offered. The term between invoicing and when payment is due is not significant. For certain products or services and customer types, we require payment before the products or services are delivered to the customer. Deferred Commissions Deferred Revenue Deferred revenue represents either customer advance payments or billings for which the aforementioned revenue recognition criteria have not yet been met. Disaggregated Revenue The Company disaggregates revenue from contracts with customers by geography and revenue generating activity, as it believes it best depicts how the nature, amount, timing and uncertainty of revenue and cash flows are affected by economic factors.
Unbilled Receivables	Unbilled Receivables

Fair Value Measurements (Tables

Fair Value Measurements (Tables)	6 Months Ended
	Jun. 30, 2024
Fair Value Disclosures [Abstract]
Schedule of Liabilities Measured at Fair Value on a Recurring Basis	Assets measured at fair value on a recurring basis are summarized below (in thousands): Fair Value Measurements at June 30, 2024 (unaudited) Level 1 Level 2 Level 3 Total Assets: Money market funds included in cash and cash equivalents $ 209,422 $ — $ — $ 209,422 Interest rate swaps — 14,933 — 14,933 Total $ 209,422 $ 14,933 $ — $ 224,355 Fair Value Measurements at December 31, 2023 Level 1 Level 2 Level 3 Total Assets: Money market funds included in cash and cash equivalents $ 211,661 $ — $ — $ 211,661 Interest rate swaps — 14,270 — 14,270 Total $ 211,661 $ 14,270 $ — $ 225,931

Goodwill and Other Intangible_2

Goodwill and Other Intangible Assets (Tables)	6 Months Ended
	Jun. 30, 2024
Goodwill and Intangible Assets Disclosure [Abstract]
Schedule of Goodwill	Changes in the Company’s goodwill balance for the six months ended June 30, 2024 are summarized in the table below (in thousands): Balance at December 31, 2023 $ 353,778 Impairment of goodwill (87,227) Foreign currency translation adjustment (2,387) Balance at June 30, 2024 $ 264,164
Schedule of Intangible Assets, Net	The following is a summary of the Company’s intangible assets, net (in thousands): Estimated Useful Gross Accumulated Net Carrying June 30, 2024: (unaudited) Customer relationships 1-10 $ 353,145 $ 220,490 $ 132,655 Trade name 1.5-10 9,446 7,696 1,750 Developed technology 4-9 86,722 68,395 18,327 Favorable Leases 6.3 271 107 164 Total intangible assets $ 449,584 $ 296,688 $ 152,896 Estimated Useful Gross Accumulated Net Carrying December 31, 2023: Customer relationships 1-10 $ 378,923 $ 222,436 $ 156,487 Trade name 1.5-10 10,012 7,862 2,150 Developed technology 4-9 94,103 70,582 23,521 Favorable Leases 6.3 280 89 191 Total intangible assets $ 483,318 $ 300,969 $ 182,349

Debt (Tables)

Debt (Tables)	6 Months Ended
	Jun. 30, 2024
Debt Disclosure [Abstract]
Schedule of Long-term Debt	Long-term debt consisted of the following at June 30, 2024 and December 31, 2023 (in thousands): June 30, 2024 December 31, 2023 Senior secured loans (includes unamortized discount of $4,288 and $5,376 based on an imputed interest rate of 7.6% and 7.6%, at June 30, 2024 and December 31, 2023, respectively) $ 475,062 $ 476,674 Less current maturities (3,313) (3,172) Total long-term debt $ 471,749 $ 473,502
Schedule of Debt, Interest Rate Swap	The impact of the Company’s derivative financial instruments on its condensed consolidated statements of comprehensive (loss) income for the three and six months ended June 30, 2024 and June 30, 2023 was as follows (in thousands): Three Months Ended June 30, Six Months Ended June 30, 2024 2023 2024 2023 Unrealized gain (loss) recognized in Other comprehensive income (loss) on interest rate swaps (956) $ 7,905 663 $ (249) Amounts reclassified from Accumulated other comprehensive income (loss) to interest expense, net (1,485) — (2,942) — Total Other comprehensive income (loss) on interest rate swaps $ (2,441) $ 7,905 $ (2,279) $ (249)

Net Loss Per Share (Tables)

Net Loss Per Share (Tables)	6 Months Ended
	Jun. 30, 2024
Earnings Per Share [Abstract]
Schedule of Computation of Loss Per Share	The following table sets forth the computations of loss per share (in thousands, except share and per share amounts): Three Months Ended June 30, Six Months Ended June 30, 2024 2023 2024 2023 Numerator: Net Loss $ (11,439) $ (15,147) $ (107,569) $ (155,192) Preferred stock dividends and accretion (1,390) (1,329) (2,765) (2,644) Net loss attributable to common stockholders $ (12,829) $ (16,476) $ (110,334) $ (157,836) Denominator: Weighted–average common shares outstanding, basic and diluted 27,348,672 32,473,872 28,133,285 32,367,084 Net loss per common share, basic and diluted $ (0.47) $ (0.51) $ (3.92) $ (4.88)
Schedule of Anti–dilutive Common Share Equivalents	Potential shares of common stock are excluded from the computation of diluted earnings per share when their effect would be antidilutive. Performance-based restricted stock units are considered dilutive when the related performance criteria have been met assuming the end of the reporting period represents the end of the performance period. All potential shares of common stock are antidilutive in periods of net loss. Potential shares of common stock not included in the computation of earnings per share because their effect would have been antidilutive or because the performance criterion was not met were as follows (in thousands): Contingently issuable shares associated with outstanding performance-based restricted stock units (each, a “PSU”) were not included in the basic earnings per share calculations for the periods presented, as the applicable vesting conditions had not been satisfied. June 30, 2024 2023 Stock options 122,530 152,683 Restricted stock units 2,716,299 2,242,054 Performance restricted stock units 350,000 193,750 Series A Preferred Stock on an if-converted basis (1) 7,140,482 6,827,998 Total anti–dilutive common share equivalents 10,329,311 9,416,485 (1) As of June 30, 2024 , the Series A Preferred Stock plus accumulated dividends totaled $125.0 million. The Series A Preferred Stock has a conversion price of $17.50 per share, as detailed in “ Note 9. Mezzanine Equity ”.

Stockholders' Equity (Tables)

Stockholders' Equity (Tables)	6 Months Ended
	Jun. 30, 2024
Equity [Abstract]
Schedule of Accumulated Other Comprehensive Income (Loss)	The following table shows the components of accumulated other comprehensive income (loss), net of income taxes, (“AOCI”) in the stockholders’ equity section of our condensed consolidated balance sheets at the dates indicated (in thousands): June 30, 2024 December 31, 2023 Foreign currency translation adjustment $ (22,766) $ (19,947) Unrealized translation loss on intercompany loans with foreign subsidiaries, net of taxes (5,000) (3,330) Unrealized gain on interest rate swaps 14,933 14,270 Realized gain on interest rate swap sale, net of amounts reclassified into interest expense, net 12,233 15,175 Total accumulated other comprehensive income (loss) $ (600) $ 6,168
Schedule of PRSU Activity	The following table summarizes PSU and RSU activity during the six months ended June 30, 2024: Number of Units Weighted-Average Grant Date Fair Value Unvested restricted units outstanding as of December 31, 2023 1,858,847 $ 9.76 Granted 2,122,687 4.13 Vested (791,414) 8.89 Forfeited (123,821) 10.17 Unvested restricted units outstanding as of June 30, 2024 3,066,299 $ 6.07
Schedule of RSU activity	The following table summarizes PSU and RSU activity during the six months ended June 30, 2024: Number of Units Weighted-Average Grant Date Fair Value Unvested restricted units outstanding as of December 31, 2023 1,858,847 $ 9.76 Granted 2,122,687 4.13 Vested (791,414) 8.89 Forfeited (123,821) 10.17 Unvested restricted units outstanding as of June 30, 2024 3,066,299 $ 6.07
Schedule of Valuation Assumptions	The range of significant assumptions used in the Monte Carlo simulation model for the PSUs granted during the six months ended June 30, 2024 was as follows: Expected volatility 74.6% - 62.06% Risk-free interest rate 4.4% - 4.0% Remaining performance period (in years) 2.73 - 2.73 Dividend yield —
Schedule of Allocated Share-Based Compensation Expense	The Company recognizes stock-based compensation expense from all awards in the following expense categories included in our condensed consolidated statements of income (in thousands): Three Months Ended June 30, Six Months Ended June 30, 2024 2023 2024 2023 Cost of revenue $ 199 $ 301 $ 385 $ 604 Research and development 638 648 1,244 1,303 Sales and marketing 362 558 759 1,134 General and administrative 3,934 4,863 6,267 9,791 Total $ 5,133 $ 6,370 $ 8,655 $ 12,832

Revenue Recognition (Tables)

Revenue Recognition (Tables)	6 Months Ended
	Jun. 30, 2024
Revenue from Contract with Customer [Abstract]
Schedule of Disaggregation of Revenue	The Company has operations primarily in the United States, United Kingdom and Canada. Information about these operations is presented below (in thousands): Three Months Ended June 30, Six Months Ended June 30, 2024 2023 2024 2023 Revenues: Subscription and support: United States $ 47,342 $ 50,162 $ 95,066 $ 102,403 United Kingdom 8,397 9,160 17,472 18,835 Canada 3,217 3,441 6,545 6,932 Other International 6,548 7,731 13,499 15,238 Total subscription and support revenue 65,504 70,494 132,582 143,408 Perpetual license: United States 879 721 1,570 1,377 United Kingdom 56 69 155 292 Canada 93 14 152 56 Other International 702 448 1,323 1,098 Total perpetual license revenue 1,730 1,252 3,200 2,823 Professional services: United States 1,212 1,557 2,445 3,155 United Kingdom 243 452 514 710 Canada 146 230 334 459 Other International 504 512 1,000 998 Total professional service revenue 2,105 2,751 4,293 5,322 Total revenue $ 69,339 $ 74,497 $ 140,075 $ 151,553

Organization and Nature of Op_2

Organization and Nature of Operations (Details)	Jun. 30, 2024 product customer
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Number of cloud software products | product	25
Number of customers | customer	10,000

Fair Value Measurements - Sched

Fair Value Measurements - Schedule of Liabilities Measured at Fair Value on a Recurring Basis (Details) - Recurring Measurement Basis - USD ($) $ in Thousands	Jun. 30, 2024	Dec. 31, 2023
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Money market funds included in cash and cash equivalents	$ 209,422	$ 211,661
Assets, Fair Value Disclosure	224,355	225,931
Interest rate swap
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Interest rate swaps	14,933	14,270
Level 1
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Money market funds included in cash and cash equivalents	209,422	211,661
Assets, Fair Value Disclosure	209,422	211,661
Level 1 | Interest rate swap
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Interest rate swaps	0	0
Level 2
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Money market funds included in cash and cash equivalents	0	0
Assets, Fair Value Disclosure	14,933	14,270
Level 2 | Interest rate swap
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Interest rate swaps	14,933	14,270
Level 3
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Money market funds included in cash and cash equivalents	0	0
Assets, Fair Value Disclosure	0	0
Level 3 | Interest rate swap
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Interest rate swaps	$ 0	$ 0

Fair Value Measurements - Narra

Fair Value Measurements - Narrative (Details) - USD ($) $ in Millions	Jun. 30, 2024	Dec. 31, 2023
Level 2 | Recurring Measurement Basis
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Debt instrument, fair value	$ 479.4	$ 482.1

Goodwill and Other Intangible_3

Goodwill and Other Intangible Assets - Schedule of Goodwill (Details) - USD ($) $ in Thousands	3 Months Ended			6 Months Ended
	Jun. 30, 2024	Mar. 31, 2024	Jun. 30, 2023	Jun. 30, 2024	Jun. 30, 2023
Goodwill [Roll Forward]
Beginning balance		$ 353,778		$ 353,778
Impairment of goodwill	$ 0	$ (87,200)	$ 0	(87,227)	$ (128,755)
Foreign currency translation adjustment				(2,387)
Ending balance	$ 264,164			$ 264,164

Goodwill and Other Intangible_4

Goodwill and Other Intangible Assets - Narrative (Details) - USD ($) $ in Thousands	3 Months Ended			6 Months Ended
	Jun. 30, 2024	Mar. 31, 2024	Jun. 30, 2023	Jun. 30, 2024	Jun. 30, 2023
Goodwill and Intangible Assets Disclosure [Abstract]
Impairment of goodwill	$ 0	$ 87,200	$ 0	$ 87,227	$ 128,755
Impairment of intangible assets (excluding goodwill)	0		0
Amortization charge of intangible assets	$ 13,500		$ 18,000	$ 27,000	$ 36,100

Goodwill and Other Intangible_5

Goodwill and Other Intangible Assets - Schedule of Intangible Assets, Net (Details) - USD ($) $ in Thousands	Jun. 30, 2024	Dec. 31, 2023
Finite-Lived Intangible Assets [Line Items]
Gross Carrying Amount	$ 449,584	$ 483,318
Accumulated Amortization	296,688	300,969
Net Carrying Amount	152,896	182,349
Customer relationships
Finite-Lived Intangible Assets [Line Items]
Gross Carrying Amount	353,145	378,923
Accumulated Amortization	220,490	222,436
Net Carrying Amount	$ 132,655	$ 156,487
Customer relationships | Minimum
Finite-Lived Intangible Assets [Line Items]
Estimated Useful Life (Years)	1 year	1 year
Customer relationships | Maximum
Finite-Lived Intangible Assets [Line Items]
Estimated Useful Life (Years)	10 years	10 years
Trade name
Finite-Lived Intangible Assets [Line Items]
Gross Carrying Amount	$ 9,446	$ 10,012
Accumulated Amortization	7,696	7,862
Net Carrying Amount	$ 1,750	$ 2,150
Trade name | Minimum
Finite-Lived Intangible Assets [Line Items]
Estimated Useful Life (Years)	1 year 6 months	1 year 6 months
Trade name | Maximum
Finite-Lived Intangible Assets [Line Items]
Estimated Useful Life (Years)	10 years	10 years
Developed technology
Finite-Lived Intangible Assets [Line Items]
Gross Carrying Amount	$ 86,722	$ 94,103
Accumulated Amortization	68,395	70,582
Net Carrying Amount	$ 18,327	$ 23,521
Developed technology | Minimum
Finite-Lived Intangible Assets [Line Items]
Estimated Useful Life (Years)	4 years	4 years
Developed technology | Maximum
Finite-Lived Intangible Assets [Line Items]
Estimated Useful Life (Years)	9 years	9 years
Favorable Leases
Finite-Lived Intangible Assets [Line Items]
Estimated Useful Life (Years)	6 years 3 months 18 days	6 years 3 months 18 days
Gross Carrying Amount	$ 271	$ 280
Accumulated Amortization	107	89
Net Carrying Amount	$ 164	$ 191

Income Taxes (Details)

Income Taxes (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2024	Jun. 30, 2023	Jun. 30, 2024	Jun. 30, 2023
Income Tax Disclosure [Abstract]
Benefit from (provision for) income taxes	$ (1,210)	$ 233	$ (663)	$ 1,655

Debt - Summary of Long-term Deb

Debt - Summary of Long-term Debt (Details) - Senior Secured Notes - USD ($) $ in Thousands	Jun. 30, 2024	Dec. 31, 2023
Debt Instrument [Line Items]
Long-term debt	$ 475,062	$ 476,674
Less current maturities	(3,313)	(3,172)
Total long-term debt	471,749	473,502
Debt instrument, unamortized discount	$ 4,288	$ 5,376
Debt instrument, imputed interest rate (percent)	7.60%	7.60%

Debt - Narrative (Details)

Debt - Narrative (Details) - USD ($) $ in Thousands	1 Months Ended		3 Months Ended		6 Months Ended
	Aug. 31, 2023	Aug. 31, 2019	Jun. 30, 2024	Jun. 30, 2023	Jun. 30, 2024	Jun. 30, 2023	Dec. 31, 2023	Dec. 31, 2019
Line of Credit Facility [Line Items]
Debt instrument, cash interest costs, percent					7.20%	5.40%
Unamortized deferred financing costs			$ 4,300		$ 4,300		$ 5,400
Interest rate swap
Line of Credit Facility [Line Items]
Unrealized gain (loss) recognized in Other comprehensive income (loss) on interest rate swaps	$ 20,500		(956)	$ 7,905	663	$ (249)
Interest rate swap | Interest Expense
Line of Credit Facility [Line Items]
Other comprehensive income (loss), derivative, excluded component, increase (decrease), before adjustments, tax			(1,500)		(2,900)
Secured Debt
Line of Credit Facility [Line Items]
Long-term debt, term		7 years
Debt instrument, face amount			$ 257,200		$ 257,200
Interest rate (percent)		5.40%
Term Loan | Secured Debt
Line of Credit Facility [Line Items]
Long-term debt, term		7 years
Interest rate (percent)			5.40%		5.40%
Floating interest rate, stated percentage			9.20%		9.20%
Credit Facility
Line of Credit Facility [Line Items]
Debt instrument, covenant compliance, percent			35%		35%
Debt instrument, covenant, leverage ratio, amount			$ 50,000		$ 50,000
Debt instrument, covenant, leverage ratio, maximum			6		6
Debt instrument, debt default, increase in interest rate on obligations upon default					2%
Credit Facility | Revolving Credit Facility
Line of Credit Facility [Line Items]
Long-term debt, term		5 years
Maximum borrowing capacity		$ 60,000	$ 60,000		$ 60,000
Line of credit facility, unused capacity, commitment fee percentage					0.50%
Credit Facility | Letter of Credit
Line of Credit Facility [Line Items]
Maximum borrowing capacity			$ 10,000		$ 10,000
Credit Facility | Secured Debt
Line of Credit Facility [Line Items]
Debt instrument, repayment rate, quarterly								0.25%
Debt instrument, repayment rate, annual								1%
Credit Facility | Secured Debt | Base Rate
Line of Credit Facility [Line Items]
Debt instrument, basis spread on variable rate					2.75%
Credit Facility | Secured Debt | Eurodollar Deposits Rate
Line of Credit Facility [Line Items]
Debt instrument, basis spread on variable rate					3.75%
Credit Facility | Secured Debt | Eurodollar Deposits Rate | Minimum
Line of Credit Facility [Line Items]
Debt instrument, basis spread on variable rate					0%
Credit Facility | Secured Debt | Federal Funds Rate
Line of Credit Facility [Line Items]
Debt instrument, basis spread on variable rate					0.50%
Credit Facility | Secured Debt | Federal Funds Rate | Minimum
Line of Credit Facility [Line Items]
Debt instrument, basis spread on variable rate					0%
Credit Facility | Secured Debt | Eurodollar
Line of Credit Facility [Line Items]
Debt instrument, basis spread on variable rate					1%

Debt - Summary of Debt, Interes

Debt - Summary of Debt, Interest Rate Swap (Details) - Interest rate swap - USD ($) $ in Thousands	1 Months Ended	3 Months Ended		6 Months Ended
	Aug. 31, 2023	Jun. 30, 2024	Jun. 30, 2023	Jun. 30, 2024	Jun. 30, 2023
Derivative Instruments, Gain (Loss) [Line Items]
Unrealized gain (loss) recognized in Other comprehensive income (loss) on interest rate swaps	$ 20,500	$ (956)	$ 7,905	$ 663	$ (249)
Amounts reclassified from Accumulated other comprehensive income (loss) to interest expense, net		(1,485)	0	(2,942)	0
Total Other comprehensive income (loss) on interest rate swaps		$ (2,441)	$ 7,905	$ (2,279)	$ (249)

Net Loss Per Share - Narrative

Net Loss Per Share - Narrative (Details) - $ / shares	Jun. 30, 2024	Dec. 31, 2023	Jul. 14, 2022
Earnings Per Share [Abstract]
Common stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Series A convertible preferred stock, par value (in dollars per share)	$ 0.0001	$ 0.0001	$ 0.0001

Net Loss Per Share - Schedule o

Net Loss Per Share - Schedule of Computation of Loss Per Share (Details) - USD ($) $ / shares in Units, $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2024	Jun. 30, 2023	Jun. 30, 2024	Jun. 30, 2023
Numerator:
Net loss	$ (11,439)	$ (15,147)	$ (107,569)	$ (155,192)
Preferred stock dividends	1,390	1,329	2,765	2,644
Net loss attributable to common stockholders, basic	(12,829)	(16,476)	(110,334)	(157,836)
Net loss attributable to common stockholders, diluted	$ (12,829)	$ (16,476)	$ (110,334)	$ (157,836)
Denominator:
Weighted-average common shares outstanding, basic (in shares)	27,348,672	32,473,872	28,133,285	32,367,084
Weighted-average common shares outstanding, diluted (in shares)	27,348,672	32,473,872	28,133,285	32,367,084
Net loss per common share, basic (in dollars per share)	$ (0.47)	$ (0.51)	$ (3.92)	$ (4.88)
Net loss per common share, diluted (in dollars per share)	$ (0.47)	$ (0.51)	$ (3.92)	$ (4.88)

Net Loss Per Share - Schedule_2

Net Loss Per Share - Schedule of Anti–dilutive Common Share Equivalents (Details) - USD ($) $ / shares in Units, $ in Millions	3 Months Ended
	Jun. 30, 2024	Jun. 30, 2023
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti–dilutive common share equivalents (in shares)	10,329,311	9,416,485
Preferred stock, conversion price (in dollars per share)	$ 17.50
Stock options
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti–dilutive common share equivalents (in shares)	122,530	152,683
Restricted stock units
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti–dilutive common share equivalents (in shares)	2,716,299	2,242,054
Performance restricted stock units
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti–dilutive common share equivalents (in shares)	350,000	193,750
Series A Preferred Stock
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti–dilutive common share equivalents (in shares)	7,140,482	6,827,998
Preferred stock accumulated dividends	$ 125

Mezzanine Equity (Details)

Mezzanine Equity (Details) $ / shares in Units, $ in Millions		6 Months Ended
	Jul. 14, 2022 USD ($) $ / shares shares	Jun. 30, 2024 USD ($) director $ / shares shares	Dec. 31, 2023 $ / shares
Temporary Equity [Line Items]
Number of shares issued (in shares) | shares	115,000
Series A convertible preferred stock, par value (in dollars per share)	$ 0.0001	$ 0.0001	$ 0.0001
Offering price per share (in dollars per share)	$ 1,000
Aggregate purchase price | $	$ 115
Stock issuance costs | $		$ 4.6
Temporary equity, liquidation preference (in dollars per share)	$ 1,000
Temporary equity dividend, closing date duration	7 years
Dividends payable | $		$ 10
Preferred stock, convertible, shares issuable | shares		569,054
Preferred stock, conversion price (in dollars per share)		$ 17.50
Temporary equity, liquidation preference | $		$ 125
Temporary equity, liquidation cash purchase price		105%
Temporary equity liquidation preference percentage		105%
Temporary equity voting power		50%
Number of board of directors to elect | director		1
Threshold for electing one board member and not the actual ownership		5%
Threshold for electing a non-voting board member requirement and not the actual ownership percentage		10%
Preferred stock, conversion price (in dollars per share)		$ 17.50
Temporary equity, number of consecutive trading days		10 days
Before Seven Year Anniversary
Temporary Equity [Line Items]
Temporary equity dividend rate percentage	4.50%
After Seven Year Anniversary
Temporary Equity [Line Items]
Temporary equity dividend rate percentage	7%

Stockholders' Equity - Narrativ

Stockholders' Equity - Narrative (Details) $ / shares in Units, $ in Thousands		3 Months Ended			6 Months Ended		12 Months Ended
	May 02, 2023 $ / shares shares	Jun. 30, 2024 USD ($) vote $ / shares shares	Mar. 31, 2024	Jun. 30, 2023 USD ($)	Jun. 30, 2024 USD ($) vote $ / shares shares	Jun. 30, 2023 USD ($)	Dec. 31, 2023 $ / shares shares	May 31, 2024 shares	Sep. 30, 2023 USD ($)
Class of Stock [Line Items]
Common stock, par value (in dollars per share) | $ / shares		$ 0.0001			$ 0.0001		$ 0.0001
Common stock, votes per share | vote		1			1
Sales and excise tax payable | $		$ 200			$ 200
Stock repurchased and retired during period, value | $		$ 2,798			$ 10,796
Tax benefit preservation plan, ownership change, threshold ownership percentage	4.90%
Preferred stock, par value (in dollars per share) | $ / shares	$ 0.0001
Share-based compensation arrangement by share-based payment award, options, outstanding, number (in shares)		122,530			122,530
PRSU and RSU
Class of Stock [Line Items]
Share-based compensation arrangement by share-based payment award, non-option equity instruments, outstanding, number (in shares)		3,066,299			3,066,299
Granted (in shares)					2,122,687
Performance restricted stock units
Class of Stock [Line Items]
Granted (in shares)					250,000		100,000
Target payout, percentage		100%			100%
Performance restricted stock units | Maximum
Class of Stock [Line Items]
Award vesting rights, percentage			300%				200%
Intercompany loans with foreign subsidiaries, accumulated tax
Class of Stock [Line Items]
Tax expense (benefit) recognized in OCI | $					$ 3,100
Intercompany loans, accumulated tax
Class of Stock [Line Items]
Tax expense (benefit) recognized in OCI | $		$ (100)		$ 500	$ (200)	$ 1,000
Preferred Stock Purchase Rights
Class of Stock [Line Items]
Class of warrant or right, dividends declared (in shares)	1
Class of warrant or right, outstanding (in shares)	27,030,605
Class of warrant or right, exercise price of warrants or rights (in dollars per share) | $ / shares	$ 15,250
Preferred stock purchase right, purchase share (in shares)	0.001
Preferred stock purchase right, purchase price adjustment percentage	1%
Class of warrant or right, entitled dividend payment per security called by each warrant or right (in dollars per share) | $ / shares	$ 0.001
Class of warrant or right, entitled liquidation payment per security called by each warrant or right (in dollars per share) | $ / shares	$ 0.001
Class of warrant or right, entitled liquidation payment, common stock equivalent, number of shares (in shares)	1
Class of warrant or right, voting power, common stock equivalent, number of shares (in shares)	1
2023 Share Repurchase Program
Class of Stock [Line Items]
Stock repurchase program, authorized amount | $									$ 25,000
Stock repurchase program, number of shares authorized to be repurchased (in shares)								6,453,805
Stock repurchases and retirements (in shares)		966,051			3,208,705
Stock repurchased and retired during period, value | $		$ 2,800			$ 11,000

Stockholders' Equity - Schedule

Stockholders' Equity - Schedule of Accumulated Other Comprehensive Income (Loss) (Details) - USD ($) $ in Thousands	Jun. 30, 2024	Mar. 31, 2024	Dec. 31, 2023	Jun. 30, 2023	Mar. 31, 2023	Dec. 31, 2022
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stockholders' equity attributable to parent	$ 6,488	$ 20,121	$ 126,294	$ 167,784	$ 166,833	$ 308,870
Accumulated Other Comprehensive Income (Loss)
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stockholders' equity attributable to parent	(600)	$ 2,307	6,168	$ 15,415	$ 4,206	$ 11,110
Foreign currency translation adjustment
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stockholders' equity attributable to parent	(22,766)		(19,947)
Unrealized translation loss on intercompany loans with foreign subsidiaries, net of taxes
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stockholders' equity attributable to parent	(5,000)		(3,330)
Unrealized gain on interest rate swaps
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stockholders' equity attributable to parent	14,933		14,270
Realized gain on interest rate swap sale, net of amounts reclassified into interest expense, net
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stockholders' equity attributable to parent	$ 12,233		$ 15,175

Stockholders' Equity - Schedu_2

Stockholders' Equity - Schedule of PRSU and RSU Activity (Details) - $ / shares	6 Months Ended	12 Months Ended
	Jun. 30, 2024	Dec. 31, 2023
PRSU and RSU
Number of Units
Unvested balances at beginning of period (in shares)	1,858,847
Granted (in shares)	2,122,687
Vested (in shares)	(791,414)
Forfeited (in shares)	(123,821)
Unvested balances at end of period (in shares)	3,066,299	1,858,847
Weighted-Average Grant Date Fair Value
Unvested balances at beginning of period (in dollars per share)	$ 9.76
Granted (in dollars per share)	4.13
Vested (in dollars per share)	8.89
Forfeited (in dollars per share)	10.17
Unvested balances at end of period (in dollars per share)	$ 6.07	$ 9.76
Performance restricted stock units
Number of Units
Granted (in shares)	250,000	100,000

Stockholders' Equity - Schedu_3

Stockholders' Equity - Schedule of Valuation Assumptions (Details) - Performance restricted stock units	6 Months Ended
	Jun. 30, 2024
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Expected volatility, minimum	74.60%
Expected volatility, maximum	62.06%
Risk-free interest rate, minimum	4.40%
Risk-free interest rate, maximum	4%
Dividend yield	0%
Minimum
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Remaining performance period (in years)	2 years 8 months 23 days
Maximum
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Remaining performance period (in years)	2 years 8 months 23 days

Stockholders' Equity - Schedu_4

Stockholders' Equity - Schedule of Allocated Share-Based Compensation Expense (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2024	Jun. 30, 2023	Jun. 30, 2024	Jun. 30, 2023
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Share-based compensation expense	$ 5,133	$ 6,370	$ 8,655	$ 12,832
Cost of revenue
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Share-based compensation expense	199	301	385	604
Research and development
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Share-based compensation expense	638	648	1,244	1,303
Sales and marketing
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Share-based compensation expense	362	558	759	1,134
General and administrative
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Share-based compensation expense	$ 3,934	$ 4,863	$ 6,267	$ 9,791

Revenue Recognition - Narrative

Revenue Recognition - Narrative (Details) - USD ($) $ in Thousands	3 Months Ended	6 Months Ended
	Jun. 30, 2024	Jun. 30, 2024	Dec. 31, 2023
Revenue from External Customer [Line Items]
Unbilled receivables	$ 3,531	$ 3,531	$ 2,701
Deferred commissions, amortization period	6 years	6 years
Deferred commissions renewal amortization period		18 months
Commissions capitalized in excess of amortization of deferred commissions	$ 300	$ 1,000
Revenue expected to be recognized from performance obligations	$ 252,700	$ 252,700
Revenue, Remaining Performance Obligation, Expected Timing of Satisfaction, Start Date [Axis]: 2024-07-01
Revenue from External Customer [Line Items]
Revenue, remaining performance obligation, percentage	69%	69%
Expected satisfaction period of performance obligations, in months	12 months	12 months
Subscription and support
Revenue from External Customer [Line Items]
Revenue recognized, previously in unearned revenue		$ 72,700
Professional services
Revenue from External Customer [Line Items]
Revenue recognized, previously in unearned revenue		$ 1,800

Revenue Recognition - Schedule

Revenue Recognition - Schedule of Disaggregation of Revenue (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2024	Jun. 30, 2023	Jun. 30, 2024	Jun. 30, 2023
Disaggregation of Revenue [Line Items]
Revenue	$ 69,339	$ 74,497	$ 140,075	$ 151,553
Subscription and support
Disaggregation of Revenue [Line Items]
Revenue	65,504	70,494	132,582	143,408
Subscription and support | United States
Disaggregation of Revenue [Line Items]
Revenue	47,342	50,162	95,066	102,403
Subscription and support | United Kingdom
Disaggregation of Revenue [Line Items]
Revenue	8,397	9,160	17,472	18,835
Subscription and support | Canada
Disaggregation of Revenue [Line Items]
Revenue	3,217	3,441	6,545	6,932
Subscription and support | Other International
Disaggregation of Revenue [Line Items]
Revenue	6,548	7,731	13,499	15,238
Perpetual license
Disaggregation of Revenue [Line Items]
Revenue	1,730	1,252	3,200	2,823
Perpetual license | United States
Disaggregation of Revenue [Line Items]
Revenue	879	721	1,570	1,377
Perpetual license | United Kingdom
Disaggregation of Revenue [Line Items]
Revenue	56	69	155	292
Perpetual license | Canada
Disaggregation of Revenue [Line Items]
Revenue	93	14	152	56
Perpetual license | Other International
Disaggregation of Revenue [Line Items]
Revenue	702	448	1,323	1,098
Professional services
Disaggregation of Revenue [Line Items]
Revenue	2,105	2,751	4,293	5,322
Professional services | United States
Disaggregation of Revenue [Line Items]
Revenue	1,212	1,557	2,445	3,155
Professional services | United Kingdom
Disaggregation of Revenue [Line Items]
Revenue	243	452	514	710
Professional services | Canada
Disaggregation of Revenue [Line Items]
Revenue	146	230	334	459
Professional services | Other International
Disaggregation of Revenue [Line Items]
Revenue	$ 504	$ 512	$ 1,000	$ 998